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

HRID 380078

반응식

HRID 380078 반응식
[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

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 127654-MethoxybenzenethiolHCID 81531DiisopropylethylamineHCID 12953535N-Boc-DL-serine Benzyl Ester

생성물 1

HCID 206933362-t-Butoxycarbonylamino-3-(4-methoxyphenylthio)propionic acid benzyl ester

시약·촉매·용매 3

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매HCID 31297Methanesulfonyl chloride용매

반응 조건

온도
4 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e60addf815e34a8d82b9412f22d8d2bf
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300514B1

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