Lithium Hydroxide → HCID 21963917, compound

HRID 2212364Notes

Reaction equation

HRID 2212364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=3[F:36])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][CH:23]([O:25]C(=O)C)[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=3[F:36])[CH2:12][CH2:13][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][CH:23]([OH:25])[CH2:22]3)(=[O:19])=[O:20])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 21048949HCID 21048949, compound

Product 1

HCID 21963917HCID 21963917, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of acetic acid 1-[4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexylmethanesulfonyl]-azetidin-3-yl ester (Example 29) (185 mg, 0.33 mmol.) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide (16 mg, 0.67 mmol.) in water (5 mL) and the mixture stirred for 45 minutes. The solvent was removed in vacuo and the residue diluted with 1N aqueous sodium hydroxide (10 mL) and extracted into ethyl acetate (2×20 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4) and evaporated to leave the desired compound (171 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with 1N aqueous sodium hydroxide (10 mL)
  3. extractionextracted into ethyl acetate (2×20 mL)
  4. washThe combined organic layers were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f259078c826748d4be0b49cdc5aa384b
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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