Sodium hydride → HCID 178514754, compound

HRID 706996Notes

Reaction equation

HRID 706996 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-7b2127884da847f3b27d7f0850e75bf7
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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