Imidazole → HCID 22827924, compound

HRID 370514Notes

Reaction equation

HRID 370514 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-595e3a7893cc442d8ecb1740705e2ccc
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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