Boc-Tyr-OMe → (S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

HRID 879690

반응식

HRID 879690 반응식
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:22][C:23]1[C:28]([CH3:29])=[C:27](B(O)O)[CH:26]=[CH:25][N:24]=1.O.CCOC(C)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:27]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:22])[C:28]=2[CH3:29])=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 7019130Boc-Tyr-OMeHCID 22728543Water ethylacetateHCID 58327508(2,3-Dimethylpyridin-4-YL)boronic acid

생성물 1

HCID 58327260(S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester수율 4.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 304 mg of (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester, 314 mg 2,3-dimethylpyridine-4-boronic acid, 374 mg cupric acetate, and 2 grams of powdered 4 Å molecular sieves in 50 mL dry DCM and 0.75 mL TEA was stirred vigorously at rt under an O2 atmosphere for 40 h. The mixture was then poured into water-EtOAc. The organic layer was washed with water and saturated brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (DCM-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (18 mg). LCMS (m/z) 401.

후처리

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (DCM-EtOAc)

출처 및 근거

ORD 기록
ord-37aeb88988e24c85973cd034d02c9e6a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987295B2

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