Lithium hydroxide, monohydrate → HCID 178521353, compound

HRID 2096208Notes

Reaction equation

HRID 2096208 reaction equation
[OH:1][C:2]1([C:29]2[S:33][C:32](S(C)(=O)=O)=[N:31][CH:30]=2)[CH2:7][CH2:6][CH:5]([N:8]2[CH2:11][CH:10]([NH:12][C:13]([CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:14])[CH2:9]2)[CH2:4][CH2:3]1.[OH:38][Li].O>O.C1COCC1>[OH:1][C:2]1([C:29]2[S:33][C:32]([OH:38])=[N:31][CH:30]=2)[CH2:7][CH2:6][CH:5]([N:8]2[CH2:9][CH:10]([NH:12][C:13]([CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=3)=[O:14])[CH2:11]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 46240784HCID 46240784, compound

Product 1

HCID 178521353HCID 178521353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-({1-[4-Hydroxy-4-(2-methanesulfonyl-thiazol-5-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (less polar isomer, 47a, 100 mg, 0.18 mmol) and LiOH hydrate (Aldrich, 15 mg, 0.36 mmol) in water (1 mL) and THF (1 mL) was heated to 60° C. in a sealed tube for 2 hours. The crude solution was directly purified by a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe crude solution was directly purified by a CombiFlash® system

Sources & evidence

ORD record
ord-dec0d6bc7e2b438cb10c5fa3aa3e9f18
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

Loading…