Acetic Acid → HCID 15702727, compound

HRID 893903Notes

Reaction equation

HRID 893903 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:33])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:9]1=[O:34])[C:5]([CH3:7])=[CH2:6])([OH:3])=[O:2].[N+](=[CH2:37])=[N-].C(O)(=O)C>O1CCCC1.C(OCC)C>[CH3:37][O:2][C:1]([CH:4]([N:8]1[CH:11]([S:12][N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])[CH:10]([NH:24][C:25](=[O:33])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:9]1=[O:34])[C:5]([CH3:7])=[CH2:6])=[O:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 54366830HCID 54366830, compound

Product 1

HCID 15702727HCID 15702727, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 14 g (29 mmoles) of 1-(1-carboxy-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one (prepared as described in Example 5 B) in 100 ml of tetrahydrofuran a solution of 35 mmoles of diazomethane in diethyl ether was added. The clear solution was treated with acetic acid to remove excess diazomethane and evaporated to dryness. After addition of 100 ml of benzene the solution was filtered, concentrated and chromatographed on a column containing 500 g of silica gel using a 4:1 (v/v) mixture of toluene and ethyl acetate as an eluent. There was obtained 1-(1-methoxycarbonyl-2-methylprop-2-enyl)-3-phenylacetamido-4-phthalimidothio-azetidin-2-one.

Workup

  1. additionwas added
  2. customto remove excess diazomethane
  3. customevaporated to dryness
  4. additionAfter addition of 100 ml of benzene the solution
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customchromatographed on a column
  8. additioncontaining 500 g of silica gel using
  9. additiona 4:1 (v/v) mixture of toluene and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-c2e4ed1c3f50489fae89ca3b1ea7cef6
Source dataset
uspto-grants-1981_08
Patent number
US04282145

Reaction notes

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