Sodium hydride → HCID 87731915, compound

HRID 2252254Notes

Reaction equation

HRID 2252254 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:41](=[CH:42][C:43]=1[OH:44])[C:8]1[N:9]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:20][CH:19]=4)=[CH:14][CH:13]=3)[C:7]=1[CH2:6]2.[H-].[Na+].C1(N[S:54]([C:57]([F:60])([F:59])[F:58])(=[O:56])=[O:55])C=CC=CC=1>C1COCC1>[F:58][C:57]([F:60])([F:59])[S:54]([O:44][C:43]1[CH:42]=[C:41]2[C:5]([CH2:6][C:7]3[C:11]([C:12]4[CH:17]=[CH:16][C:15]([C:18]5[CH:19]=[CH:20][C:21]([O:24][CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:22][CH:23]=5)=[CH:14][CH:13]=4)=[N:10][N:9]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:8]=32)=[CH:4][C:3]=1[O:2][CH3:1])(=[O:56])=[O:55]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 69199103HCID 69199103, compound

Product 1

HCID 87731915HCID 87731915, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of Example 267H (1.29 g, 2.04 mmol) in THF (10 mL) at room temperature was added 95% NaH (51.6 mg, 2.04 mmol). The mixture was stirred for half an hour, and N-phenyltrifluoromethane sulphonamide (0.88 g, 2.45 mmol) was added. The reaction mixture was stirred at 40° C. overnight. The reaction mixture was purified by flash chromatography to give the desired product (1.80 g, 100%). MS (APCI) m/z 763 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at 40° C. overnight
  2. customThe reaction mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-3aea3f115a514478b1b1ffb3243d9f96
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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