tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate → (1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinate

HRID 1759712노트

반응식

HRID 1759712 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[CH3:2].[Br:26][C:27]1[CH:28]=[C:29]([F:38])[C:30]2[O:34][C:33](SC)=[N:32][C:31]=2[CH:37]=1>C([O-])(=O)C.C([O-])(=O)C.[Hg+2]>[Br:26][C:27]1[CH:28]=[C:29]([F:38])[C:30]2[O:34][C:33]([NH:15][C@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])=[CH:24][CH:23]=3)=[N:32][C:31]=2[CH:37]=1

참가 물질

4

반응물 2

HCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 225994905-Bromo-7-fluoro-2-(methylthio)-benzoxazole

생성물 1

HCID 69880648(1,1-dimethyl ethyl) N-(5-bromo-7-fluoro-2-benzoxazolyl)-O-(4-ethoxy-4-oxo-butyl)-L-tyrosinate수율 40.5%

시약·촉매·용매 1

HCID 15337Mercuric acetate촉매

반응 조건

온도
100 °C

실험 절차

The mixture constituted by aminoester 4-2 (865 mg; 2.46 mmoles), 5-bromo-7-fluoro-2-(methylthio)-benzoxazole (804 mg; 3.07 mmoles) and mercury diacetate (437 mg) is agitated for 3 hours, under nitrogen and at 100° C. After cooling down, the medium is chromatographed eluting with a CH2Cl2/ethyl acetate mixture 95/5, 564 mg of expected product is obtained, which is repurified by recrystallizing from isopropyl oxide. 528 mg of purified product is obtained.

후처리

  1. temperatureAfter cooling down
  2. customthe medium is chromatographed
  3. washeluting with a CH2Cl2/ethyl acetate mixture 95/5

출처 및 근거

ORD 기록
ord-57cb84ae0b3540efbaee501e8b58cb22
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06838453B2

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