Hydrochloric Acid → 2-t-Butoxycarbonylamino-3-(4-methoxyphenylthio)propionic acid benzyl ester

HRID 380078Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:21])[CH:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N(C(C)C)CC)(C)C.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([SH:40])=[CH:36][CH:35]=1>ClCCl.C(N(CC)CC)C.S(Cl)(C)(=O)=O>[CH2:1]([O:8][C:9](=[O:21])[CH:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][S:40][C:37]1[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 4 °C

Procedure

To a solution of 2-t-butoxycarbonylamino-3-hydroxypropionic acid benzyl ester (29.5 g) in dichloromethane (300 ml), triethylamine (21 ml) and mesyl chloride (8.6 ml) were added and the reaction solution was stirred for 30 minutes at 4° C. The reaction solution was added to 1 N hydrochloric acid cooling with ice. The obtained yellow oil was dissolved into dichloromethane (300 ml), and diisopropylethylamine (17 ml) and 4-methoxybenzenethiol (12 ml) were added thereto at 4° C. and the reaction solution was stirred for 3 hours at room temperature and concentrated. The residue was purified by column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (24.8 g) having the following physical data.

Workup

additionwere added
stirringat 4° C. and the reaction solution was stirred for 3 hours at room temperature
concentrationconcentrated
customThe residue was purified by column chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record: ord-e60addf815e34a8d82b9412f22d8d2bf
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300514B1

Reaction notes

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