3-(Trifluoromethyl)phenylboronic acid → HCID 58717675、化合物

HRID 1784231ノート

反応式

HRID 1784231 の反応式
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]

参加物

4

反応物 3

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 68706663HCID 68706663、化合物HCID 68862985HCID 68862985、化合物

生成物 1

HCID 58717675HCID 58717675、化合物収率 44.8%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-17f2b40259684ceeaa4d720cb6a5b410
出典データセット
uspto-grants-2009_03
特許番号
US07501538B2

反応ノート

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