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

HRID 1784231Notes

Reaction equation

HRID 1784231 reaction equation
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]

Participants

4

Reactant 3

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 68706663HCID 68706663, compoundHCID 68862985HCID 68862985, compound

Product 1

HCID 58717675HCID 58717675, compoundYield 44.8%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-17f2b40259684ceeaa4d720cb6a5b410
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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