Hydrochloric Acid → HCID 11951430, compound

HRID 661009Notes

Reaction equation

HRID 661009 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[CH3:15])=[CH:12][CH:13]=1)=[O:8].[OH-].[Na+].Cl>CO>[F:31][C:29]([F:30])([F:32])[C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH:14]([C:11]3[S:10][C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[O:8])=[CH:13][CH:12]=3)[CH3:15])=[CH:22][CH:21]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67485082HCID 67485082, compound

Product 1

HCID 11951430HCID 11951430, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-({5-[1-(4′-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (chiral Isomer 1) (170 mg, 0.356 mmol) in methanol (7.1 mL) is treated with 5N NaOH (0.712 mL) and shaken at rt for 2 h. The reaction is neutralized with 1N HCl (0.748 mL), and extracted into ethyl acetate (2×). The combined organic layers are dried and concentrated, giving the title compound (142 mg). MS (ES): 464.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-44395e14ed2c4a489a0797dcdfc345cc
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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