N-(2-chloro-4-nitrobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester → N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

HRID 1060424노트

반응식

HRID 1060424 반응식
[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[CH:21][CH:20]=1)[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[Cl:16]>CO.[Ni]>[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[CH:21][CH:20]=1)[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[Cl:16]

참가 물질

4

반응물 1

HCID 53828542N-(2-chloro-4-nitrobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

생성물 1

HCID 54392214N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester수율 91.1%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

Ra—Ni (0.4 mL of 50% dispersion in water) was added to a solution of N-(2-chloro-4-nitrobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (1.04 g) in anhydrous MeOH (50 mL) and the mixture was stirred at room temperature under H2 atmosphere for 3.5 h. The mixture was then filtered over Celite and washed with MeOH. The filtrate was evaporated and the residue was purified by flash column chromatography (silica gel; eluent: CH2Cl2/MeOH 100:1 to 20:1) to give N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (887 mg). ESMS: m/z 439 (MH+). The product obtained above was also prepared via the coupling of 4-(2-methoxyphenyl)-L-phenylalanine methyl ester hydrochloride with 4-amino-2-chlorobenzoic acid using EDC and HOBT in an analogous manner as described in Example 2.

후처리

  1. filtrationThe mixture was then filtered over Celite
  2. washwashed with MeOH
  3. customThe filtrate was evaporated
  4. customthe residue was purified by flash column chromatography (silica gel; eluent: CH2Cl2/MeOH 100:1 to 20:1)

출처 및 근거

ORD 기록
ord-df289dc40dd949cbb800f49160df3322
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521666B1

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