Methyl thiazolidine-2-carboxylate hydrochloride → HCID 53941519, compound

HRID 1872185Notes

Reaction equation

HRID 1872185 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[NH:10][CH2:9][CH2:8][S:7]1)=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])=[CH:15]2>ClCCl.CN(C)C=O>[CH3:2][O:3][C:4]([CH:6]1[N:10]([C:25](=[O:26])[CH2:24][NH:23][C:21]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([Cl:11])=[CH:20][CH:19]=3)=[O:22])[CH2:9][CH2:8][S:7]1)=[O:5]

Participants

4

Reactant 2

HCID 2737506Methyl thiazolidine-2-carboxylate hydrochlorideHCID 11436686N-[(5-chloro-1H-indol-2-yl)carbonyl]glycine

Product 1

HCID 53941519HCID 53941519, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

(±)-Thiazolidine-2-carboxylic acid methyl ester hydro-chloride (1.02 mmol) and [(5-chloro-1H-indole-2-carbonyl)-amino]-acetic acid (1.02 mmol) were coupled according to Procedure A (1:1 dichloromethane-dimethylformamide solvent) and the crude product triturated with 1:1 ether-hexanes giving a light yellow solid. Yield 79%; HPLC (60/40) 4.47 minutes (95%); TSPMS 382/384 (MH+, 100%).

Workup

  1. customthe crude product triturated with 1:1 ether-hexanes giving a light yellow solid
  2. customHPLC (60/40) 4.47 minutes (95%)

Sources & evidence

ORD record
ord-9d592212093f457188f3ae7b6d11c796
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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