Iodoethane → HCID 20037725, compound

HRID 1904635Notes

Reaction equation

HRID 1904635 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:19])[CH2:6][N:7]([C:13](=[O:18])[CH:14]([CH3:17])[CH2:15][SH:16])[CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:3].[CH2:20](I)[CH3:21]>C(O)C>[CH2:2]([O:4][C:5](=[O:19])[CH2:6][N:7]([C:13](=[O:18])[CH:14]([CH3:17])[CH2:15][S:16][CH2:20][CH3:21])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1)[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 5360545SodiumHCID 20037727HCID 20037727, compound

Product 1

HCID 20037725HCID 20037725, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 0.45 g (0.02M) of sodium in 50 ml ethanol was dropwise added a solution of 4.8 g of N-(3-mercapto-2-methyl propanoyl)-N-cyclopentyl glycine ethyl ester in 10 ml ethanol and stirring continued for 1 hour. Then, 3.04 g (0.02M) ethyl iodide in 5 ml ethanol was added and stirring continued for 4 hours. The solution was concentrated in vacuum, diluted with ether, washed with water, dried over MgSO4 and evaporated to dryness. The oily residue was chromatographed by HPLC using EtOAc-hexane (3:17) as eluent.

Workup

  1. stirringstirring
  2. waitcontinued for 4 hours
  3. concentrationThe solution was concentrated in vacuum
  4. additiondiluted with ether
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe oily residue was chromatographed by HPLC

Sources & evidence

ORD record
ord-869026a184e54e55a26aefc59a49c882
Source dataset
uspto-grants-1989_06
Patent number
US04839367

Reaction notes

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