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

HRID 1066050Notes

Reaction equation

HRID 1066050 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-87bdcae14c8f4efdba94b434c8006b46
Source dataset
uspto-grants-2001_06
Patent number
US06242422B1

Reaction notes

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