Lithium Hydroxide → HCID 69583707, compound

HRID 2212360Notes

Reaction equation

HRID 2212360 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[S:10]([CH2:13][CH:14]1[CH2:19][CH2:18][C:17]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:16][CH2:15]1)(=[O:12])=[O:11])=[O:4].[OH-].[Li+]>O1CCCC1.O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([C:17]2([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[F:27])[CH2:18][CH2:19][CH:14]([CH2:13][S:10]([N:6]3[CH2:7][CH2:8][CH2:9][C@@H:5]3[C:3]([OH:4])=[O:2])(=[O:11])=[O:12])[CH2:15][CH2:16]2)(=[O:30])=[O:29])=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69583984HCID 69583984, compound

Product 1

HCID 69583707HCID 69583707, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-1-[4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexylmethanesulfonyl]-pyrrolidine-2-carboxylic acid methyl ester (Example 18) (108 mg, 0.19 mmol.) in tetrahydrofuran (10 mL) was added lithium hydroxide (18 mg) in water (4 mL) and the mixture vigorously stirred for 1.5 hours. After removal of the solvent in vacuo, the aqueous residue was acidified to pH 1 with 2N aqueous hydrochloric acid and extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica, eluting with ethyl acetate:dichloromethane:acetic acid (30:60:1), to afford the desired MS (ES+) 562 ([MH]+).

Workup

  1. customAfter removal of the solvent in vacuo
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave a residue which
  7. customwas purified by column chromatography on silica
  8. washeluting with ethyl acetate:dichloromethane:acetic acid (30:60:1)
  9. customto afford the desired MS (ES+) 562 ([MH]+)

Sources & evidence

ORD record
ord-78f10788d3b64afbb25d44d969634941
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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