Hydrochloric Acid → HCID 59355976, compound

HRID 661014Notes

Reaction equation

HRID 661014 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH:14]([O:18][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)=[C:21]([CH3:37])[CH:20]=2)[CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=1)=[O:8].[Li+].[OH-].Cl>O1CCCC1>[CH3:25][C:23]1[CH:24]=[C:19]([O:18][CH:14]([C:11]2[S:10][C:9]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:38])=[O:2])=[O:8])=[CH:13][CH:12]=2)[CH:15]([CH3:17])[CH3:16])[CH:20]=[C:21]([CH3:37])[C:22]=1[C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([F:35])([F:34])[F:36])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59355972HCID 59355972, compound

Product 1

HCID 59355976HCID 59355976, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-({5-[1-(2,6-Dimethyl-4′-trifluoromethoxy-biphenyl-4-yloxy)-2-methyl-propyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (Isomer 2) in tetrahydrofuran (2.0 mL) is added 1 N LiOH (2.0 mL) and stirred overnight. The reaction mixture is acidified with 1 N HCl (2.2 mL) and extracted with EtOAc (3×10 mL). Combined extracts are dried over MgSO4, filtered, and concentrated to provide 3-({5-[1-(2,6-dimethyl-4′-trifluoromethoxy-biphenyl-4-yloxy)-2-methyl-propyl]-thiophene-2-carbonyl}-amino)-propionic acid (Isomer 2) (0.101 g, 89%) as a white foam. MS (ES): 536.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialCombined extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1c6d0282cd674668bfb6719069a424fd
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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