Sodium bis(trimethylsilyl)amide → 7-[[4-(1-(tert-Butyldimethylsilanyloxy)hexyl)benzyl]methanesulfonylamino]-heptanoic Acid Ethyl Ester

HRID 606546Notes

Reaction equation

HRID 606546 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:13][C:14](=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH3:12].[C:27]([Si:31]([O:34][CH:35]([C:41]1[CH:46]=[CH:45][C:44]([CH2:47]I)=[CH:43][CH:42]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>C1COCC1>[CH2:11]([O:13][C:14](=[O:26])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH2:47][C:44]1[CH:43]=[CH:42][C:41]([CH:35]([O:34][Si:31]([C:27]([CH3:28])([CH3:30])[CH3:29])([CH3:32])[CH3:33])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:46][CH:45]=1)(=[O:23])=[O:24])[CH3:12]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 12150839Ethyl 7-(methanesulfonamido)heptanoateHCID 67046121HCID 67046121, compound

Product 1

HCID 670466937-[[4-(1-(tert-Butyldimethylsilanyloxy)hexyl)benzyl]methanesulfonylamino]-heptanoic Acid Ethyl EsterYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium bis(trimethylsilyl)amide (1.0 mL of a 1.0 M solution in THF, 1.00 mmol) was added to a solution of the sulfonamide 4 (220 mg, 0.88 mmol) in THF (2.2 mL) at 0° C. The reaction was warmed to room temperature and a solution of the iodide 9 (432 mg, 1.00 mmol) in THF (3.0 mL) was added. The reaction was stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 4:1 hex/EtOAc) gave 159 mg (29%) of the silyl ether 10 as a light yellow viscous oil.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic portion was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6bf537f3d3547b5a297cf451ad41925
Source dataset
uspto-grants-2011_03
Patent number
US07915316B2

Reaction notes

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