Dimethylformamide → HCID 70605223, compound

HRID 1448402Notes

Reaction equation

HRID 1448402 reaction equation
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:14][N:13]=[N:12][N:11]=3)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.CN(C)C=O.C(N(CC)CC)C.[C:29]([O:35][CH2:36]Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>O>[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[N:11]=[N:12][N:13]([CH2:36][O:35][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[N:14]=3)[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]12

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 178431949HCID 178431949, compound

Product 1

HCID 70605223HCID 70605223, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 2.40 g. of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam in 15 ml. of N,N-dimethylformamide, is added 2.8 ml. of triethylamine. Stirring is continued for a further 15 minutes, and then 2.68 g. of chloromethyl pivalate is added. The mixture is stirred at ambient temperature for 5 hours, and then it is diluted with 100 ml. of water. It is then extracted with ethyl acetate. The extract is washed with water, dried using anhydrous sodium sulfate, and then it is evaporated in vacuo to give a mixture of the title compounds. The individual isomers are obtained by chromatographic separation of the crude product.

Workup

  1. additionTo a stirred suspension of 2.40 g
  2. stirringThe mixture is stirred at ambient temperature for 5 hours
  3. additionit is diluted with 100 ml
  4. extractionIt is then extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. customit is evaporated in vacuo
  8. customto give

Sources & evidence

ORD record
ord-530bc9f4ef394c07bca6ce9bec7208a7
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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