Benzaldehyde → Methyl (4R)-2-phenyl-1,3-thiazolidine-4-carboxylate

HRID 1371294Notes

Reaction equation

HRID 1371294 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][SH:8])[NH2:6].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCCC1>[C:11]1([CH:10]2[NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][S:8]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 2733208L-Cysteine, methyl ester, hydrochloride

Product 1

HCID 14790915Methyl (4R)-2-phenyl-1,3-thiazolidine-4-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of L-cysteine methyl ester hydrochloride (1.717 g, 10 mmol) in tetrahydrofuran (5.0 mL) at room temperature under nitrogen was added benzaldehyde (1.02 mL, 10 mmol) followed by triethylamine (4.2 mL, 30 mmol). After stirring at room temperature for 3.5 hrs, the resulting mixture was filtered through a pad of silica gel eluting with EtOAc. Evaporation of the filtrate gave the title compound (1.95 g, 88%) as a colorless oil. TLC(EtOAc-hexane; 1:5) Rf=0.22.

Workup

  1. filtrationthe resulting mixture was filtered through a pad of silica gel eluting with EtOAc
  2. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-2194b992c06a4819a26c6ca96d373f8c
Source dataset
uspto-grants-2007_01
Patent number
US07157430B2

Reaction notes

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