3-(Trifluoromethyl)phenylboronic acid → HCID 58717675, 화합물

HRID 1784231노트

반응식

HRID 1784231 반응식
C[O:2][C:3](=[O:31])[C@@H:4]([NH:13][C:14]([C:16]1[CH:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=2)[CH:19]=[CH:20][C:21]=1[OH:22])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1.[Li+].[OH-].O.C1COCC1.CO>>[Cl:30][C:25]1[CH:24]=[C:23]([C:18]2[CH:19]=[CH:20][C:21]([OH:22])=[C:16]([C:14]([NH:13][C@@H:4]([CH2:5][C:6]3[CH:7]=[CH:8][C:9]([C:38]4[CH:37]=[CH:36][CH:35]=[C:34]([C:33]([F:44])([F:43])[F:32])[CH:39]=4)=[CH:10][CH:11]=3)[C:3]([OH:2])=[O:31])=[O:15])[CH:17]=2)[CH:28]=[CH:27][C:26]=1[F:29]

참가 물질

4

반응물 3

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 68706663HCID 68706663, 화합물HCID 68862985HCID 68862985, 화합물

생성물 1

HCID 58717675HCID 58717675, 화합물수율 44.8%

실험 절차

The resin-bound 3-(4-bromo-phenyl)-(2S)-2-[(3′-chloro-4′-fluoro -4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic acid methyl ester (100 mg, 0.3 mmol) was reacted with 3-trifluoromethyl-phenylboronic acid (285 mg, 1.5 mmol) by following Procedure K. The resulting resin-bound methyl ester was hydrolyzed with LiOH/H2O/THF/methanol, and washed with DMF, MeOH, DCM (three times of each). The title compound was then cleaved from the resin with TMSBr/TFA/DCM (1:1:5) at rt for 4 h. The residue obtained after removing the solvent was purified by column chromatography to give 75 mg of the title compound.

후처리

  1. washwashed with DMF, MeOH, DCM (three times of each)
  2. customThe residue obtained
  3. customafter removing the solvent
  4. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-17f2b40259684ceeaa4d720cb6a5b410
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501538B2

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