Hydrochloric Acid → HCID 11951964, compound

HRID 661010Notes

Reaction equation

HRID 661010 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[C:22]([CH3:36])[CH:21]=2)[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=1)=[O:8].[OH-].[Na+].Cl>CO>[CH3:16][C:15]([CH3:18])([CH3:17])[CH:14]([C:11]1[S:10][C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[O:8])=[CH:13][CH:12]=1)[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)=[C:22]([CH3:36])[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67484494HCID 67484494, compound

Product 1

HCID 11951964HCID 11951964, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-({5-[2,2-dimethyl-1-(2-methyl-4′-trifluoromethyl-biphenyl-4-yloxy)-propyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (chiral Isomer 1) (36 mg, 0.067 mmol) in methanol (1.0 mL) is treated with 5N NaOH (0.067 mL) and shaken at rt overnight. The reaction is neutralized with 1N HCl (0.068 mL), and extracted into ethyl acetate (2×). The combined organic layers are dried and concentrated, giving the title compound (21.6 mg). MS (ES): 520.3 [M+H]+.

Workup

  1. extractionextracted into ethyl acetate (2×)
  2. customThe combined organic layers are dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-77c78c6064be4915b459f8c77dbf4127
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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