Hydrochloric Acid → HCID 46940803, compound

HRID 1095867Notes

Reaction equation

HRID 1095867 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:33])[C:20]([OH:32])([C:25]3[CH:30]=[N:29][C:28]([CH3:31])=[CH:27][N:26]=3)[C:21]([F:24])([F:23])[F:22])=[C:15]([Cl:34])[CH:14]=2)=[CH:7][CH:6]=1)C.[Li+].[OH-].Cl>O1CCCC1.CO>[Cl:34][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[CH:19]([CH3:33])[C:20]([OH:32])([C:25]1[CH:30]=[N:29][C:28]([CH3:31])=[CH:27][N:26]=1)[C:21]([F:24])([F:22])[F:23])[O:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:35])=[O:3])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46940553HCID 46940553, compound

Product 1

HCID 46940803HCID 46940803, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-{3-chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(5-methyl-pyrazin-2-yl)-propyl]-phenoxymethyl}-benzoic acid ethyl ester (Example 1, 130 mg, 0.26 mmol) in tetrahydrofuran (2.5 ml) and methanol (0.5 ml) was added a 1 M aqueous LiOH solution (0.31 ml). The mixture was stirred for 4 h at 60° C. (bath temperature). The cooled mixture was acidified with 1 M aqueous HCl. Tetrahydrofuran and methanol were evaporated in vacuo. To the suspension water was added. The precipitation was filtered, washed with water and dried to give the title compound as a white solid (105 mg). MS (m/e, ISP neg. ion)=479.4 [M−H+].

Workup

  1. customTetrahydrofuran and methanol were evaporated in vacuo
  2. additionTo the suspension water was added
  3. customThe precipitation
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-13e39c97b78c49b4b92fafbc5112141a
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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