3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 3-(Biphenyl-4-yl)-(2S)-[(3'-chloro-4'-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic Acid Methyl Ester

HRID 2373779노트

반응식

HRID 2373779 반응식
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:18][C:19](=[O:28])[C:20]1[CH:25]=[C:24](Br)[C:23](O)=[CH:22][CH:21]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Cl:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=1[F:37].C[Si](Br)(C)C.C(O)(C(F)(F)F)=[O:47].C(Cl)Cl>>[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:18][C:19]([C:20]1[CH:21]=[C:22]([C:33]2[CH:34]=[CH:35][C:36]([F:37])=[C:31]([Cl:30])[CH:32]=2)[CH:23]=[CH:24][C:25]=1[OH:47])=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

참가 물질

4

반응물 3

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 692051283-(biphenyl-4-yl)-(2S)-(5-bromo-4-hydroxy-benzoylamino)-propionic acid methyl esterHCID 86597135TMSBr TFA DCM

생성물 1

HCID 113865603-(Biphenyl-4-yl)-(2S)-[(3'-chloro-4'-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic Acid Methyl Ester

실험 절차

The resin-bound 3-(biphenyl-4-yl)-(2S)-(5-bromo-4-hydroxy-benzoylamino)-propionic acid methyl ester (50 mg, 0.3 mmol) was reacted with 3-chloro-4-fluorophenylboronic acid (240 mg, 1.5 mmol) following general procedure D, cleaved with TMSBr/TFA/DCM (1:1:5) at rt for 4 h. The residue obtained after removing the solvent was purified by chromatography to give 35 mg of title compound.

후처리

  1. customThe residue obtained
  2. customafter removing the solvent
  3. customwas purified by chromatography

출처 및 근거

ORD 기록
ord-937c882b8d5c438cb8e446fa8bc2c15f
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459472B2

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