Sodium hydride → HCID 178514754, compound

HRID 2040262Notes

Reaction equation

HRID 2040262 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[Cl:17][C:18]1[CH:19]=[C:20]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F.[H-].[Na+]>O1CCCC1>[Cl:17][C:18]1[CH:19]=[C:20]([S:25]([NH2:28])(=[O:26])=[O:27])[CH:21]=[CH:22][C:23]=1[O:16][CH2:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([OH:8])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75098833-Chloro-4-fluorobenzenesulfonamideHCID 178455322HCID 178455322, compound

Product 1

HCID 178514754HCID 178514754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Trans-4-(tert-butyldimethylsilyloxy)cyclohexyl)methanol (275 mg, prepared according to a procedures in WO 2008/124878) and 3-chloro-4-fluorobenzenesulfonamide (259 mg) in tetrahydrofuran (15 mL) were treated with sodium hydride (180 mg, 60%) overnight. The reaction was quenched with water (1 mL) and trifluoroacetic acid (4 mL) was added. The resulting mixture was stirred for 1 hour and concentrated. The residue was triturated with water and methanol to provide the title compound.

Workup

  1. customThe reaction was quenched with water (1 mL) and trifluoroacetic acid (4 mL)
  2. additionwas added
  3. concentrationconcentrated
  4. customThe residue was triturated with water and methanol

Sources & evidence

ORD record
ord-24f8c9190aee49818fbb727d4995af7d
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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