Carbon tetrabromide → N-(2,6-dichlorobenzoyl)-4-[2-(bromomethyl)phenyl]-L-phenylalanine methyl ester

HRID 24648노트

반응식

HRID 24648 반응식
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29]O)=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].C(Br)(Br)(Br)[Br:33].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][Br:33])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53694008N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl ester

생성물 1

HCID 54266682N-(2,6-dichlorobenzoyl)-4-[2-(bromomethyl)phenyl]-L-phenylalanine methyl ester수율 70.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl ester (0.15 g), CBr4 (0.22 g) and PPh3 (0.173 g) in CH2Cl2 (5 mL) was stirred at room temperature for 18 h. The solvent was evaporated and the residue was purified by flash column chromatography (silica gel; eluent: CH2Cl2/EtOAc 9:1 to 8:1) to yield 0.12 g of N-(2,6-dichlorobenzoyl)-4-[2-(bromomethyl)phenyl]-L-phenylalanine methyl ester. ESMS: m/z 522 (MH+).

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash column chromatography (silica gel; eluent: CH2Cl2/EtOAc 9:1 to 8:1)

출처 및 근거

ORD 기록
ord-efef225ddc214e9a9a1cfee3daa05c51
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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