Iodoethane → HCID 22827923, compound

HRID 1632268Notes

Reaction equation

HRID 1632268 reaction equation
[CH2:1](N(C(C)C)C(C)C)[CH3:2].[OH:10][C@@H:11]([C@H:13]1[C:19](=[O:20])[N:18]2[CH:14]1[S:15][C:16](=[S:34])[CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22])[CH3:12].ICC>O1CCCC1>[CH2:1]([S:34][C:16]1[S:15][CH:14]2[N:18]([C:19](=[O:20])[C@@H:13]2[C@H:11]([OH:10])[CH3:12])[C:17]=1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 22827924HCID 22827924, compound

Product 1

HCID 22827923HCID 22827923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.200 ml of ethyl diisopropylamine was added to 0.426 g of 4-nitrobenzyl 6(S)-[1(R)-hydroxyethyl]-7-oxo-3-thioxo-4-thia-1-azabicyclo[3,2,0]heptane-2-carboxylate in dry tetrahydrofuran with stirring. 0.252 ml of iodoethane was then added and stirring was continued for 16 hours at room temperature. The reaction mixture was then evaporated to dryness and chromatographed on silica gel, eluting with ethyl acetate/hexane mixtures, to give the title product as a mixture of 5R and 5S isomers.

Workup

  1. stirringstirring
  2. customThe reaction mixture was then evaporated to dryness
  3. customchromatographed on silica gel
  4. washeluting with ethyl acetate/hexane mixtures

Sources & evidence

ORD record
ord-66e6081f96604d7f94003fddfcb27115
Source dataset
uspto-grants-1984_10
Patent number
US04474793

Reaction notes

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