Methyl-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate → Methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)propanoate

HRID 724713노트

반응식

HRID 724713 반응식
[CH3:1][O:2][C:3](=[O:25])[C:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[C:8]([CH3:13])[CH:7]=1>C(O)C.[B-](F)(F)(F)F.COC1C([P@](CC[P@](C2C=CC=CC=2)C2C(OC)=CC=CC=2)C2C=CC=CC=2)=CC=CC=1.C1CC=CCCC=C1.[Rh]>[CH2:18]([O:17][C:15]([NH:14][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[C:8]([CH3:13])[CH:7]=1)[C:3]([O:2][CH3:1])=[O:25])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

4

반응물 1

HCID 69597784Methyl-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate

생성물 1

HCID 11596601Methyl (2S)-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)propanoate수율 83.3%

시약·촉매·용매 2

HCID 10930696(1Z,5Z)-cycloocta-1,5-diene;(R)-(2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane;rhodium;tetrafluoroborate촉매HCID 702Ethanol용매

실험 절차

A solution of methyl-2-[(benzyloxy)carbonyl]amino-3-(4-bromo-3-methylphenyl)acrylate (10.4 g, 0.0257 mol) in ethanol (200 mL) was degassed with nitrogen. (R,R)-(−)-1,2-bis[(o-methoxyphenyl)(phenyl)phosphino]ethane(1,5-cyclooctadiene) rhodium (I) tetrafluroborate (194 mg, 257 μmol) was added to the reaction solution and nitrogen was bubble through. After five cycles of vacuum/H2, the reaction was heated at a pressure of 50 psi of hydrogen at room temperature. After 24 h, the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography to yield the desired product (8.7 g, 83%). 1H NMR (400 MHz, CD3OD): δ 7.40 (d, 1H), 7.3 (m, 5H), 7.13 (s, 1H), 6.91 (m, 1H), 5.00 (m, 2H), 4.42 (m, 1H), 3.70 (s, 3H), 3.09 (m, 1H), 2.84 (m, 1H), 2.32 (s, 3H); MF=C19H20BrNO4; LCMS found for C19H20BrNO4Na (M+Na)+: m/z=428, 430.

후처리

  1. customwas bubble through
  2. customthe solvent was removed under reduced pressure
  3. customThe crude residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-d16d8de212384be5ac12c67fcd9d1aa8
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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