Salicylaldehyde → ethyl (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylate

HRID 979963

Reaction equation

[CH2:1]([O:3][C:4](=[O:9])[C@H:5]([CH2:7][SH:8])[NH2:6])[CH3:2].[CH:10](=O)[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13]>>[C:4]([C@@H:5]1[CH2:7][S:8][CH:10]([C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[OH:13])[NH:6]1)([O:3][CH2:1][CH3:2])=[O:9]

Participants

Reactant 2

HCID 6998Salicylaldehyde

HCID 13359Ethyl L-cysteinate

Product 1

HCID 54389765ethyl (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylate

Procedure

The procedure of M. Schubert (J. Biol. Chem., 114, 341 (1936)) was used to prepare 57 starting from L-cysteine ethyl ester and salicylaldehyde. Purification by silica gel chromatography afforded 57 as a thick oil. TLC (silica gel; 3:1 cyclohexane-EtOAc) showed a mixture of 2 isomers, Rf=0.4, 0.5. IR (film): 3300 (sharp), 3000, 1740, 1430 cm-1. NMR (CCl4): 1.28 (3H, t, J=7); 2.9-3.5 (2H, m); 3.8-4.4 (3H, m); 5.50, 5.80 (1H, 2x broad s); 6.5-7.3 (4H, m).

Workup

customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-6a760e3cbe3a449aa263b091a4747684
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04634715

Linked notes

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