Hydrochloric Acid → HCID 44601404, compound

HRID 888506Notes

Reaction equation

HRID 888506 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][C:13]=2[CH2:25][S:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:8]=[C:7]([Cl:32])[CH:6]=1.[OH-].[Li+].Cl>C1COCC1.O.CO>[Cl:32][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][C:13]=2[CH2:25][S:26][CH2:27][C:28]([F:30])([F:31])[F:29])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58372758HCID 58372758, compound

Product 1

HCID 44601404HCID 44601404, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To {3-chloro-5-[4-(2,2-dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester (0.038 g, 0.08 mmol) in THF:H2O:MeOH (2:1:2; 2 mL) was added 1N aqueous lithium hydroxide, and the mixture was stirred at room temperature overnight. The mixture was acidified to pH 5 with 10% aqueous HCl, and extracted with EtOAc. The crude material was purified by preparative HPLC to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-0b5ef27b5aed42e58e8373442e112bc7
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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