Hydrochloric Acid → HCID 11951968, compound

HRID 661016Notes

Reaction equation

HRID 661016 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH:14]([O:17][C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:27][CH:26]=3)=[C:20]([CH3:35])[CH:19]=2)[CH2:15][CH3:16])=[CH:12][CH:13]=1)=[O:8].[OH-].[Na+].Cl>CO>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([C:21]2[C:20]([CH3:35])=[CH:19][C:18]([O:17][CH:14]([C:11]3[S:10][C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[O:8])=[CH:13][CH:12]=3)[CH2:15][CH3:16])=[CH:23][C:22]=2[CH3:24])=[CH:26][CH:27]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67484850HCID 67484850, compound

Product 1

HCID 11951968HCID 11951968, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-({5-[1-(4′-tert-butyl-2,6-dimethyl-biphenyl-4-yloxy)-propyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (Isomer 2) (90.2 mg, 0.178 mmol) in methanol (1.8 mL) is treated with 5N NaOH (0.178 mL) and shaken at rt overnight. The reaction is neutralized with 1N HCl (0.182 mL), and extracted into ethyl acetate (2×). The combined organic layers are dried and concentrated, giving the title compound (70.5 mg). MS (ES): 494.3 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-6e508cc5e22640068b9578d82df7496a
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

Loading…