(+)-Thalidomide
Cat. No. B015901
M. Wt: 258.23 g/mol
InChI Key: UEJJHQNACJXSKW-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
Patent
US05877200
Procedure details
A stirred mixture of N-phthaloyl-L-glutamine (48.0 g, 174 mmoL), carbonyldiimidazole (30.43 g, 188 mmoL), and 4-dimethylaminopyridine (0.105 g, 0.861 mmoL) in anhydrous tetrahydrofuran (300 mL) is heated to reflux for 16 hours. The reaction slurry is filtered and the solid washed with methylene chloride (200 mL). The solid is air-dried and then dried in vacuo (60° C., <1 mm) to afford 40.40 g (90%) of thalidomide as a white powder. 1HNMR (DMSO-d6) δ 11.16 (s, 1 H, NH), 8.05-7.80 (br s, 4 H, Ar), 5.18 (dd, 1 H, J=12, 5 Hz, CHCO), 3.05-2.85 (m, 1 H, CH2CO), 2,70-2.45 (m, 2 H, CH2CH 2), 2.15-2.00 (M, 1 H, CH2). 13C NMR (DMSO-d6) δ 172.8, 169.8, 167.1, 134.9, 131.2, 123.4, 49.0, 30.9, 22.0.
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([C@H:12]([C:18]([OH:20])=O)[CH2:13][CH2:14][C:15]([NH2:17])=[O:16])[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH:2]1[CH:1]=[CH:6][C:5]2[C:7](=[O:8])[N:9]([CH:12]3[C:18](=[O:20])[NH:17][C:15](=[O:16])[CH2:14][CH2:13]3)[C:10](=[O:11])[C:4]=2[CH:3]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
48 g
|
|
Type
|
reactant
|
|
Smiles
|
C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CCC(=O)N)C(=O)O
|
|
Name
|
|
|
Quantity
|
30.43 g
|
|
Type
|
reactant
|
|
Smiles
|
C(=O)(N1C=NC=C1)N1C=NC=C1
|
|
Name
|
|
|
Quantity
|
0.105 g
|
|
Type
|
catalyst
|
|
Smiles
|
CN(C1=CC=NC=C1)C
|
|
Name
|
|
|
Quantity
|
300 mL
|
|
Type
|
solvent
|
|
Smiles
|
O1CCCC1
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
is heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux for 16 hours
|
|
Duration
|
16 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The reaction slurry is filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
the solid washed with methylene chloride (200 mL)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solid is air-dried
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried in vacuo (60° C., <1 mm)
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C=1C=CC2=C(C1)C(=O)N(C2=O)C3CCC(=O)NC3=O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 40.4 g | |
| YIELD: PERCENTYIELD | 90% | |
| YIELD: CALCULATEDPERCENTYIELD | 90% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US05877200
Procedure details
A stirred mixture of N-phthaloyl-L-glutamine (48.0 g, 174 mmoL), carbonyldiimidazole (30.43 g, 188 mmoL), and 4-dimethylaminopyridine (0.105 g, 0.861 mmoL) in anhydrous tetrahydrofuran (300 mL) is heated to reflux for 16 hours. The reaction slurry is filtered and the solid washed with methylene chloride (200 mL). The solid is air-dried and then dried in vacuo (60° C., <1 mm) to afford 40.40 g (90%) of thalidomide as a white powder. 1HNMR (DMSO-d6) δ 11.16 (s, 1 H, NH), 8.05-7.80 (br s, 4 H, Ar), 5.18 (dd, 1 H, J=12, 5 Hz, CHCO), 3.05-2.85 (m, 1 H, CH2CO), 2,70-2.45 (m, 2 H, CH2CH 2), 2.15-2.00 (M, 1 H, CH2). 13C NMR (DMSO-d6) δ 172.8, 169.8, 167.1, 134.9, 131.2, 123.4, 49.0, 30.9, 22.0.
Identifiers
|
REACTION_CXSMILES
|
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([C@H:12]([C:18]([OH:20])=O)[CH2:13][CH2:14][C:15]([NH2:17])=[O:16])[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C1C=CN=CC=1.O1CCCC1>[CH:2]1[CH:1]=[CH:6][C:5]2[C:7](=[O:8])[N:9]([CH:12]3[C:18](=[O:20])[NH:17][C:15](=[O:16])[CH2:14][CH2:13]3)[C:10](=[O:11])[C:4]=2[CH:3]=1
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
48 g
|
|
Type
|
reactant
|
|
Smiles
|
C1=CC=C2C(=C1)C(=O)N(C2=O)[C@@H](CCC(=O)N)C(=O)O
|
|
Name
|
|
|
Quantity
|
30.43 g
|
|
Type
|
reactant
|
|
Smiles
|
C(=O)(N1C=NC=C1)N1C=NC=C1
|
|
Name
|
|
|
Quantity
|
0.105 g
|
|
Type
|
catalyst
|
|
Smiles
|
CN(C1=CC=NC=C1)C
|
|
Name
|
|
|
Quantity
|
300 mL
|
|
Type
|
solvent
|
|
Smiles
|
O1CCCC1
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
is heated
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
to reflux for 16 hours
|
|
Duration
|
16 h
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
The reaction slurry is filtered
|
WASH
|
Type
|
WASH
|
|
Details
|
the solid washed with methylene chloride (200 mL)
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solid is air-dried
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried in vacuo (60° C., <1 mm)
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C=1C=CC2=C(C1)C(=O)N(C2=O)C3CCC(=O)NC3=O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 40.4 g | |
| YIELD: PERCENTYIELD | 90% | |
| YIELD: CALCULATEDPERCENTYIELD | 90% |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
