Methanol → HCID 66919040, compound

HRID 1367491Notes

Reaction equation

HRID 1367491 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])(=[O:13])=[O:12])[CH2:8][C@H:7]1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:5])C.CO.O.[OH-].[Li+]>O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:11]([CH:9]1[CH2:10][C@@H:6]([C:4]([OH:5])=[O:3])[C@H:7]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[CH2:8]1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 66919101HCID 66919101, compound

Product 1

HCID 66919040HCID 66919040, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (1R,2R)-4-(2-Chloro-benzenesulfonyl)-2-(4-chloro-phenoxymethyl)-cyclopentanecarboxylic acid ethyl ester (epimeric mixture, 132 mg) in tetrandrofuran (2.4 mL), methanol (0.6 mL) and water (1.2 mL) was added lithium hydroxide monohydrate (14 mg). The mixture was stirred at 80° C. for 2.5 h then concentrated in vacuo. The residue was dissolved in water and the pH was adjusted to 1 with hydrochloric acid (2N). The precipitate was filtered, washed with water and dried in vacuo to afford the title compound (103 mg, 83%) as a white solid. MS (EI): 446.1 (M+NH4)+.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ce552541e64648e59d9f77ee6bfeadbb
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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