(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester → N-t-butyloxycarbonyl-3-amino-l-tyrosine methyl ester

HRID 1358597

반응식

HRID 1358597 반응식
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:21]([O-])=O)[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([NH2:21])[CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

참가 물질

4

반응물 1

HCID 15518593(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester

생성물 1

HCID 15518594N-t-butyloxycarbonyl-3-amino-l-tyrosine methyl ester수율 82.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of N-(tert-butoxycarbonyl)-3-nitro-L-tyrosine methyl ester (2.0 g) and 10% Pd-C (1.0 g) in MeOH (10 ml) was subjected to catalytic hydrogenolysis at atmospheric pressure. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was triturated with ether to give 3-amino-N-(tert-butoxycarbonyl)-L-tyrosine methyl ester (1.5 g) as a solid. To a solution of the obtained compound (1.0 g) in CH2Cl2 (10 ml) was added 2,6-dichlorobenzoyl chloride (0.74 g) and DIEA (1.1 g) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluent; 2:1, Hexane/AcOEt) to give N-(tert-butoxycarbonyl)-3-(2,6-dichlorobenzamido)-L-tyrosine methyl ester (1.2 g). The obtained compound was treated in a similar manner as described in R. Example 4 to give 3-[(2,6-Dichlorobenzoyl)amino]-L-tyrosine methyl ester, hydrochloride salt.

후처리

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with ether

출처 및 근거

ORD 기록
ord-1eb0510d234b4460a49b7bd96b1b638b
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596752B1

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