2-Oxazolidinone → 2(R)-(4-thiazolylmethyl)butanedioic acid

HRID 1737116Notes

Reaction equation

C([O:5][C:6](=[O:34])[CH2:7][C@@H:8]([CH2:28][C:29]1[N:30]=[CH:31][S:32][CH:33]=1)[C:9](N[C@@H](CC1CCCCC1)[C@@H](O)[C@@H](O)CC(C)C)=[O:10])(C)(C)C.[O:35]1CCNC1=O.[OH-].[Li+].OO>>[S:32]1[CH:33]=[C:29]([CH2:28][C@H:8]([CH2:7][C:6]([OH:5])=[O:34])[C:9]([OH:10])=[O:35])[N:30]=[CH:31]1

Participants

Reactant 3

HCID 739492-Oxazolidinone

HCID 700767764-{[1(S)-(Cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxo-3(R)-(4-thiazolylmethyl)butanoic acid tert-butyl ester

HCID 86600400Lithium hydroxide hydrogen peroxide

Product 1

HCID 228615512(R)-(4-thiazolylmethyl)butanedioic acid

Procedure

4-{[1(S)-(Cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxo-3(R)-(4-thiazolylmethyl)butanoic acid tert-butyl ester: The latter 2-oxazolidinone derivative (4.02 g, 10.5 mmol) was reacted with lithium hydroxide-hydrogen peroxide according to the procedure of example 2, section (g) to give the monoprotected dicarboxylic acid of formula 2, i.e. the 4-tert-butyl ester of 2(R)-(4-thiazolylmethyl)butanedioic acid. Subsequent coupling of the latter compound (2.83 g, 10.4 mmol) with 2(S)-amino-1-cyclohexyl-6-methyl-3(R),4(S)-heptanediol hydrochloride (3.21 g, 11.5 mmol) according to the coupling procedure of example 2, section (g) gave the desired protected amido acid as a white solid (3.75 g, 72%); 1H NMR(CDCl3) δ8.70 (s, 1H), 7.10 (s,1H), 5.96 (d, J=8.3 Hz,1H), 4.40-4.25 (m,2H), 3.40-2.70 (m,6H), 2.40 (dd, J=4.4 Hz,16.8 Hz,1H), 1.95-1.10 (m,17H), 1.40 (s,9H), 0.90 (d, J=6.6 Hz,3H), 0.80 (d, J=6.4 Hz,3H).

Sources & evidence

ORD record: ord-de810f3348274ed8901b14ae28eb6f74
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541163

Reaction notes

Loading…