Synthesis routes of (R)-Warfarin

(R)-Warfarin

Número de catálogo B565621

: 5543-58-8

Peso molecular: 308.3 g/mol

Clave InChI: PJVWKTKQMONHTI-OAHLLOKOSA-N

Atención: Solo para uso de investigación. No para uso humano o veterinario.

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Patent

US06054711

Procedure details

To show that non-binding compounds do not significantly influence the FT-IR spectrum of a biological macromolecule when mixed with the biological macromolecule, 3 μg of NMT was mixed with 10 μg each of Bacitracin (trace 1), Erythromycin (2), Fusidic Acid (3) and a fungal extract (4) and a differential FT-IR spectrum of each sample was obtained (FIG. 3). The non-binding compounds did not alter the spectrum of NMT. However, a nonspecific binding compound, Warfarin (60 μg), did produce a detectable peak shift for NMT.

Name

Bacitracin

Quantity

10 μg

Type

reactant

Reaction Step One

Name

Erythromycin

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

Fusidic Acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

Warfarin

Identifiers

REACTION_CXSMILES

[CH3:1][CH2:2][C@@H:3]([C@@H]1NC(=O)[C@@H](CCCN)NC(=O)[C@@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@H]2N=C([C@@H](N)[C@H](CC)C)SC2)=O)CC(C)C)=O)CCC(O)=O)=O)[C@H](CC)C)=O)CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](CC2NC=NC=2)NC(=O)[C@@H](CC2C=CC=CC=2)NC1=O)C.CC[C@H]1OC(=O)[C@H](C)[C@@H]([O:120][C@@H:121]2[O:126][C@@H:125]([CH3:127])[C@H:124](O)[C@@:123]([O:130]C)(C)[CH2:122]2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@@](O)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@@]1(O)C.C[C@@H:153]1[C@H:162]([OH:163])[CH2:161][CH2:160][C@@:159]2(C)[C@H:154]1[CH2:155][CH2:156][C@:157]1(C)[C@@]3(C)C[C@H](OC(C)=O)/C(=C(\C(O)=O)/CCC=C(C)C)/[C@@H]3C[C@@H](O)[C@H:158]12>>[CH3:153][C:162]([CH2:161][CH:160]([C:122]1[C:121](=[O:120])[O:126][C:125]2[CH:127]=[CH:3][CH:2]=[CH:1][C:124]=2[C:123]=1[OH:130])[C:159]1[CH:158]=[CH:157][CH:156]=[CH:155][CH:154]=1)=[O:163]

Inputs

Step One

Name	Bacitracin
Quantity	10 μg
Type	reactant
Smiles	CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC=4C=CC=CC4

Name	Erythromycin
Quantity	0 (± 1) mol
Type	reactant
Smiles	CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O

Name	Fusidic Acid
Quantity	0 (± 1) mol
Type	reactant
Smiles	C[C@H]1[C@@H]2CC[C@]3([C@H]([C@]2(CC[C@H]1O)C)[C@@H](C[C@@H]\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)O)C

Conditions

Other

Conditions are dynamic	1
Details	See reaction.notes.procedure_details.

Workups

ADDITION

Type	ADDITION
Details	mixed with the biological macromolecule, 3 μg of NMT

EXTRACTION

Type	EXTRACTION
Details	a fungal extract (4)

CUSTOM

Type	CUSTOM
Details	a differential FT-IR spectrum of each sample was obtained (FIG. 3)

Outcomes

Product

Name	Warfarin
Type	product
Smiles	CC(=O)CC(C=1C=CC=CC1)C2=C(C=3C=CC=CC3OC2=O)O

Measurements

Type	Value	Analysis
AMOUNT: MASS	60 μg

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

US06054711