Hydrochloric Acid → 3-Azido-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

HRID 1154916Notes

Reaction equation

HRID 1154916 reaction equation
[Si]([N:8]1[CH:11]([CH2:12][C:13](=[O:25])[CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH:10]([N:26]=[N+:27]=[N-:28])[C:9]1=[O:29])(C(C)(C)C)(C)C.Cl>CO.O>[N:26]([CH:10]1[CH:11]([CH2:12][C:13](=[O:25])[CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[NH:8][C:9]1=[O:29])=[N+:27]=[N-:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20563674N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl-2-oxopropyl)azetidin-2-one

Product 1

HCID 205636593-Azido-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl-2-oxopropyl)azetidin-2-one (1.0 g) in methanol (10 ml) is treated with conc. hydrochloric acid (0.1 ml) and left at room temperature for 2 hr. The solution is diluted with water and extracted with ethyl acetate. The extracts are washed with 5% sodium bicarbonate solution and brine, dried, and evaporated under vacuum. The residue is chromatographed on silica gel to give 3-azido-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts are washed with 5% sodium bicarbonate solution and brine
  3. customdried
  4. customevaporated under vacuum
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-f890e91beaee4dea8a4f7c73a269ffb5
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

Loading…