Acetic Acid → HCID 54321043, compound

HRID 436034Notes

Reaction equation

HRID 436034 reaction equation
[C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[CH:10]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:35])[C:5]([CH3:7])=[CH2:6])([OH:3])=[O:2].[N+](=[CH2:38])=[N-].C(O)(=O)C>O1CCCC1.C(OCC)C>[CH3:38][O:2][C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[CH:10]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:35])[C:5]([CH3:7])=[CH2:6])=[O:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 54504252HCID 54504252, compound

Product 1

HCID 54321043HCID 54321043, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.4 g (4.8 mmoles) of 1-(1-carboxy-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one in 20 ml of tetrahydrofuran was added a solution of 6 mmoles of diazomethane in diethyl ether. The clear solution was treated with acetic acid to remove excess diazomethane and was concentrated to a small volume. After addition of diethyl ether the formed precipitate was filtered off and dried to obtain 1.9 g (3.7 mmoles or 76% yield) of 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one.

Workup

  1. customto remove excess diazomethane
  2. concentrationwas concentrated to a small volume
  3. additionAfter addition of diethyl ether the formed precipitate
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-e50a404ec04549988ae1a5f85f7b89e6
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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