Carbon tetrabromide → Methyl 4-bromo-2-(tert-butoxycarbonylamino)butanoate

HRID 254359노트

반응식

HRID 254359 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:35])[C@H:23]([CH2:32][CH2:33]O)[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(Br)(Br)(Br)[Br:37]>C(Cl)Cl>[CH3:20][O:21][C:22](=[O:35])[CH:23]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:32][CH2:33][Br:37]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10561607Methyl N-(tert-butoxycarbonyl)-L-homoserinate

생성물 1

HCID 6857808Methyl 4-bromo-2-(tert-butoxycarbonylamino)butanoate수율 20.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of triphenylphosphine (2.20 g, 8.39 mmol) in dry CH2Cl2 (20 mL) was added dropwise via syringe to a solution of N-Boc homoserine methyl ester 80 (8.39 mmol) and carbon tetrabromide (4.18 g, 12.60 mmol) in dry CH2Cl2 (20 mL). The resulting dark solution was stirred at room temperature for 16 h. Hexanes was added and precipitates were removed by suction filtration. The filtrate was concentrated under reduced pressure and subject to flash silica gel column chromatography using ethyl acetate/hexanes (1:10, v/v then 1:6, v/v) to give the desired product 90 as a yellow oil (501 mg, 20% overall yield from homoserine). 1H NMR (300 MHz, CDCl3) δ 1.45 (s, 9H), 2.12-2.48 (m, 2H), 3.39-3.47 (m, 2H), 3.78 (s, 3H), 4.33-4.48 (m, 1H), 5.10-5.22 (m, 1H). m/z (ESI) 296 [C10H18BrNO4+H]+.

후처리

  1. customprecipitates
  2. customwere removed by suction filtration
  3. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-add68f3ba04d421aabbf4ca7a99f38e9
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875619B2

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