Imidazole → HCID 22827924, compound

HRID 1980646Notes

Reaction equation

HRID 1980646 reaction equation
C([S:4][C:5]1[S:11][CH:10]2[N:7]([C:8](=[O:15])[C@@H:9]2[C@H:12]([OH:14])[CH3:13])[C:6]=1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17])(=O)C.N1C=CN=C1>O1CCOCC1.O.Cl>[OH:14][C@@H:12]([C@H:9]1[C:8](=[O:15])[N:7]2[CH:10]1[S:11][C:5](=[S:4])[CH:6]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17])[CH3:13]

Participants

6

Reactant 2

HCID 795ImidazoleHCID 22827922HCID 22827922, compound

Product 1

HCID 22827924HCID 22827924, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 0.039 g of 4-nitrobenzyl 3-acetylthio-6(S)-(1(R)-hydroxyethyl)-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-en-2-carboxylate in a mixture of 1.5 ml of dioxan and 0.15 ml of water was added 0.0069 g of imidazole at room temperature. After 5 minutes the mixture was diluted with 3 ml of 1M hydrochloric acid and 5 ml of water, and then extracted into ethyl acetate. The combined organic extracts were washed with water and dried over magnesium sulphate. The resulting solution was evaporated to give a mixture of the 5R and 5S isomers of the title compound as a foam.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulphate
  4. customThe resulting solution was evaporated
  5. customto give

Sources & evidence

ORD record
ord-379c860b628342ef8ec99fc8cc3e1e56
Source dataset
uspto-grants-1985_04
Patent number
US04510086

Reaction notes

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