Sodium Hydroxide → HCID 66582484, compound

HRID 1972490Notes

Reaction equation

HRID 1972490 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C@@H:11]([CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH:30]2[CH2:35][C:36]([O-:38])=[O:37])[CH2:10]1)(=[O:8])=[O:7].[OH-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:24])([F:25])[F:23])=[CH:17][CH:16]=2)[C@@H:11]([CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH:30]2[CH2:35][C:36]([OH:38])=[O:37])[CH2:10]1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86670365HCID 86670365, compound

Product 1

HCID 66582484HCID 66582484, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 25-mL round-bottomed flask was charged with (4-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-morpholinyl)acetate (70 mg, 0.116 mmol, Example 113), is aqueous 10 M NaOH (0.5 mL, 5.00 mmol) and MeOH (5 mL) and stirred at room temperature for 2 h. The reaction was concentrated to give (4-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-morpholinyl)acetic acid (65 mg) as a mixture of four isomers. This material was used crude in the next reaction.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-a2f96aad50534ad884a5e78ea9da944e
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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