Synthesis routes of Troglitazone

Troglitazone

カタログ番号 B1681588

: 97322-87-7

分子量: 441.5 g/mol

InChIキー: GXPHKUHSUJUWKP-UHFFFAOYSA-N

注意: 研究専用です。人間または獣医用ではありません。

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Patent

US05104888

Procedure details

Following the procedure described in Preparation 58, 120 mg of 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-ylmethoxy)benzyl]thiazolidine -2,4-dione (prepared as described in Example 32) were dissolved in 4 ml of methanol and, in the presence of 40 mg of 10% w/w palladium-on-carbon, it was reduced under 3-5 atmospheres (about 3-5 bars) pressure of hydrogen, to give the title compound. The melting point and nuclear magnetic resonance spectrum of this compound accorded with those of the compound obtained in Example 27(b).

Name

5-[4-(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-ylmethoxy)benzyl]thiazolidine -2,4-dione

Quantity

120 mg

Type

reactant

Reaction Step One

[H][H]

Name

hydrogen

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

methanol

Quantity

4 mL

Type

solvent

Reaction Step Three

Name

palladium-on-carbon

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Three

Name

title compound

Identifiers

REACTION_CXSMILES

[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH:6]=[CH:5]2.[H][H]>CO.[Pd]>[OH:1][C:2]1[C:3]([CH3:31])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][CH2:5]2

Inputs

Step One

Name	5-[4-(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-ylmethoxy)benzyl]thiazolidine -2,4-dione
Quantity	120 mg
Type	reactant
Smiles	OC=1C(=C2C=CC(OC2=C(C1C)C)(C)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)C

Step Two

[H][H]

Name	hydrogen
Quantity	0 (± 1) mol
Type	reactant
Smiles	[H][H]

Step Three

Name	methanol
Quantity	4 mL
Type	solvent
Smiles	CO

Name	palladium-on-carbon
Quantity	0 (± 1) mol
Type	solvent
Smiles	[Pd]

Conditions

Other

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

Outcomes

Product

Name	title compound
Type	product
Smiles	OC=1C(=C2CCC(OC2=C(C1C)C)(C)COC1=CC=C(CC2C(NC(S2)=O)=O)C=C1)C

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.