Sodium hydride → 6-t-Butoxycarbonylamino-4-N-(carbomethoxymethyl)-perhydro-1,4-thiazepin-5-one

HRID 1981889Notes

Reaction equation

HRID 1981889 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][NH:11][C:10]1=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH2:18][C:19]([O:21][CH3:22])=[O:20].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][N:11]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:10]1=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6429536Methyl IodoacetateHCID 15591256(Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester

Product 1

HCID 136337326-t-Butoxycarbonylamino-4-N-(carbomethoxymethyl)-perhydro-1,4-thiazepin-5-oneYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-t-Butoxycarbonylamino-perhydro-1,4-thiazepin-5-one (0.1 g) and methyl iodoacetate (0.1 g) are dissolved in 1 ml of THF. Sodium hydride (50% suspension in oil) is added in batches. After one hour at room temperature, the reaction is quenched with 2 ml of 10% ammonium chloride solution. The crude product is extracted into methylene chloride, and subsequently chromatographed on silica gel (40:1 chloroform-methanol) to yield the pure product (0.09 g). The NMR spectrum is consistent with the assigned structure. A sample is obtained by recrystallization from ether-methanol and analyzes for C13H22N2O5S.

Workup

  1. customthe reaction is quenched with 2 ml of 10% ammonium chloride solution
  2. extractionThe crude product is extracted into methylene chloride
  3. customsubsequently chromatographed on silica gel (40:1 chloroform-methanol)

Sources & evidence

ORD record
ord-636097863177492da31dfa4e441736f9
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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