Hydrochloric Acid → HCID 58717675, compound

HRID 2373795Notes

Reaction equation

HRID 2373795 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]([NH:22][C:23]([C:25]1[CH:26]=[C:27]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([Cl:39])[CH:33]=2)[CH:28]=[CH:29][C:30]=1[OH:31])=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:8][CH:7]=1.[Li+].[OH-].C(OCC)(=O)C.Cl>C1COCC1.CO>[Cl:39][C:34]1[CH:33]=[C:32]([C:27]2[CH:28]=[CH:29][C:30]([OH:31])=[C:25]([C:23]([NH:22][C@@H:4]([CH2:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=4)=[CH:8][CH:7]=3)[C:3]([OH:40])=[O:2])=[O:24])[CH:26]=2)[CH:37]=[CH:36][C:35]=1[F:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 10483156HCID 10483156, compound

Product 1

HCID 58717675HCID 58717675, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(S)-[(3′-Chloro-4′-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-3-(3′-trifluoromethyl-biphenyl-4-yl)-propionic acid methyl ester (3.0 g, 5.2 mmol) was dissolved in 100 mL of THF-methanol (4-1), cooled to 0° C. and 20 mL 2N LiOH added. The reaction was stirred at 0° C. for 1 hour. Ethyl acetate (100 mL) and 1N HCl (100 mL) were added to the mixture and the organic washed with brine, dried and evaporated to give 2-(S)-[(3′-chloro-4′-fluoro-4-hydroxy-biphenyl-3-carbonyl)-amino]-3-(3′-trifluoromethyl-biphenyl-4-yl)-propionic acid (2.8 g). LC/MS (m/z): 558 [(M+1)+].

Workup

  1. washthe organic washed with brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-a93986ca38e94cf288c6faf2445fdf25
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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