Iodoethane → HCID 22827923, compound

HRID 1980648Notes

Reaction equation

HRID 1980648 reaction equation
[CH:1](NC(C)C)(C)[CH3:2].[OH:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[CH:12]1[S:13][C:14](=[S:32])[CH:15]2[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])[CH3:10].ICC>O1CCCC1>[CH2:1]([S:32][C:14]1[S:13][CH:12]2[N:16]([C:17](=[O:18])[C@@H:11]2[C@H:9]([OH:8])[CH3:10])[C:15]=1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 7912DiisopropylamineHCID 22827924HCID 22827924, compound

Product 1

HCID 22827923HCID 22827923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.200 ml of 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-dfe7832a5a0649e0b6b7b6c05041ed45
Source dataset
uspto-grants-1985_04
Patent number
US04510086

Reaction notes

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