Sodium hydride → HCID 21475079, compound

HRID 2294745Notes

Reaction equation

HRID 2294745 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C@H:5]([CH2:14][SH:15])[NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2].[H-].[Na+].Br[CH2:20][CH:21]1[CH2:23][CH2:22]1>CN(C)C=O>[CH:21]1([CH2:20][S:15][CH2:14][CH:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 7068955HCID 7068955, compound

Product 1

HCID 21475079HCID 21475079, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

14.7 g (59 mmol) of N-Boc-L-cysteine ethyl ester dissolved in 300 ml of dimethylformamide are added dropwise at 0° to a suspension of 2.49 g (64.8 mmol) of sodium hydride (60% in oil) in 200 ml of dimethylformamide and the mixture is stirred at 0° for 30 minutes. Subsequently, 8.37 g (62 mmol) of bromomethylcyclopropane in 30 ml of dimethylformamide are added dropwise thereto. The solution is stirred at room temperature overnight. The dimethylformamide is evaporated under reduced pressure, the residue is partitioned between ether and water and the aqueous phase is extracted 4 times with ether. The combined organic phases are washed twice with water and twice with saturated sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on silica gel using a 1:19 mixture of ethyl acetate and hexane as the eluent. There are obtained 8.4 g of tert-butyl rac-[2-[(cyclopropylmethyl)thio]-1-(ethoxycarbonyl)ethyl]carbamate as a colourless oil, MS: 304 (M+H)+.

Workup

  1. stirringThe solution is stirred at room temperature overnight
  2. customThe dimethylformamide is evaporated under reduced pressure
  3. customthe residue is partitioned between ether and water
  4. extractionthe aqueous phase is extracted 4 times with ether
  5. washThe combined organic phases are washed twice with water and twice with saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customFor purification
  9. customthe residue is chromatographed on silica gel using
  10. additiona 1:19 mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-8250cdcb84a146cd98f9df8a45e23b36
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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