HCID 20037735, compound → HCID 20037730, compound

HRID 1904637Notes

Reaction equation

HRID 1904637 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:14](=[O:19])[CH:15]([CH3:18])[CH2:16]Br)[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[S:21](C#N)[C:22]#[N:23].[K]>O.C(O)C>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:14](=[O:19])[CH:15]([CH3:18])[CH2:16][S:21][C:22]#[N:23])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 20037735HCID 20037735, compoundHCID 86630333HCID 86630333, compound

Product 1

HCID 20037730HCID 20037730, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2 g of N(3-bromo-2-methyl-propanoyl)-N-cyclopentyl glycine-t-butyl ester, 0.7 g potassium thiocyanide in 5 ml water and 40 ml ethanol was stirred and refluxed for 16 hours. After removal of the solvent, it was diluted with water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated to dryness. The oily residue was purified by HPLC using 20% EtOAc-hexane as eluent giving pure N(3-thiocyano-2-methyl propanoyl)-N-cyclopentyl glycine-t-butyl ester.

Workup

  1. temperaturerefluxed for 16 hours
  2. customAfter removal of the solvent, it
  3. additionwas diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated to dryness
  7. customThe oily residue was purified by HPLC

Sources & evidence

ORD record
ord-ca0fc04f1dad40039e3b97890670e402
Source dataset
uspto-grants-1989_06
Patent number
US04839367

Reaction notes

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