Hydrochloric Acid → HCID 44601404, compound

HRID 656759Notes

Reaction equation

HRID 656759 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-bbce05f459dc456a8397d0d1bfe59083
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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