Tetrahydrofuran → HCID 54109413, compound

HRID 1706532Notes

Reaction equation

HRID 1706532 reaction equation
O1CCCC1.C(N(CC)CC)C.[C:13]([CH:16]([N:20]1[CH2:23][CH:22]([NH:24][C:25](=[O:33])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]1=[O:34])[CH:17]([CH3:19])[CH3:18])(O)=[O:14].ClC(OCC)=O.[N-:41]=[N+:42]=[N-:43].[Na+]>O>[N:41]([C:13]([CH:16]([N:20]1[CH2:23][CH:22]([NH:24][C:25](=[O:33])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]1=[O:34])[CH:17]([CH3:19])[CH3:18])=[O:14])=[N+:42]=[N-:43]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran3×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 13859055HCID 13859055, compound

Product 1

HCID 54109413HCID 54109413, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A tetrahydrofuran solution (5 ml) containing triethylamine (1.02 g) was added to a tetrahydrofuran solution (40 ml) containing 1-(1-carboxy-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (3.04 g) at -20° C. with stirring. To this solution, there was dropwise added a tetrahydrofuran solution (5 ml) containing ethyl chloroformate (1.14 g) at -10° C. in the course of 5 minutes, whereafter the mixture was stirred at -10° to 0° C. for 2 hours. To the resultant mixture, there was all at once added water (8 ml), in which sodium azide (1.23 g) was dissolved at the same temperature, and the stirring was continued for additional half an hour. The reaction mixture was poured into ice-water (200 ml) and the resultant mixture was extracted with three portions of 100 ml methylene chloride. The extracts were washed with three portions of 100 ml water and dried over calcium chloride. The solution was evaporated to dryness under reduced pressure to give oily 1-(1-azidocarbonyl-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (3.0 g).

Workup

  1. stirringwhereafter the mixture was stirred at -10° to 0° C. for 2 hours
  2. waitthe stirring was continued for additional half an hour
  3. extractionthe resultant mixture was extracted with three portions of 100 ml methylene chloride
  4. washThe extracts were washed with three portions of 100 ml water
  5. dry with materialdried over calcium chloride
  6. customThe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ef9ed871d7e4498f9f7fe0ddaffb77de
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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