Potassium Carbonate → 3-[(Phenylacetyl)amino]-2-azetidinone

HRID 1706519Notes

Reaction equation

HRID 1706519 reaction equation
C(OC([N:9]1[CH2:12][CH:11]([NH:13][C:14](=[O:22])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:23])C(C)C)(=O)C.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CO.O>[C:16]1([CH2:15][C:14]([NH:13][CH:11]2[CH2:12][NH:9][C:10]2=[O:23])=[O:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 54233342HCID 54233342, compound

Product 1

HCID 132120483-[(Phenylacetyl)amino]-2-azetidinoneYield 58.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(1-Acetoxy-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (13.8 g.) was dissolved in a solution of methanol (100 ml.) and water (100 ml.). Potassium carbonate (6 g.) and sodium borohydride (1.65 g.) were added to said solution under ice-cooling, and the mixture was subjected to reaction at 20° C. for an hour. The precipitated crystals were collected by filtration, washed with water and dried to give 3-(2-phenylacetamido)-2-azetidinone (5.15 g.). Furthermore, the same compound (1.35 g.) was recovered from the filtrate. Total yield was 6.5 g. Mp 191° to 193° C.

Workup

  1. temperaturecooling
  2. customthe mixture was subjected to reaction at 20° C. for an hour
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ed22cdb03bcc40f4825d26d26b381cf4
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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