Hydrochloric Acid → HCID 131711543, compound

HRID 971416Notes

Reaction equation

HRID 971416 reaction equation
[C:1]([CH:4]1[O:10][CH:9]2[C:6]([C:32](=[O:40])[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:7](=[O:31])[N:8]2[C:11](=[C:28]([CH3:30])[CH3:29])[C:12]([O:14][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[NH:5]1)([OH:3])=O.C(Cl)(=O)[C:42]([Cl:44])=O.[N+](=CC(C1OC2C(C(=O)CC3C=CC=CC=3)(C(=O)N2C(=C(C)C)C(OC(C2C=CC=CC=2)C2C=CC=CC=2)=O)N1)=O)=[N-].Cl>C1C=CC=CC=1.CN(C)C=O.CCOCC>[Cl:44][CH2:42][C:1]([CH:4]1[O:10][CH:9]2[C:6]([C:32](=[O:40])[CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:7](=[O:31])[N:8]2[C:11](=[C:28]([CH3:30])[CH3:29])[C:12]([O:14][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[NH:5]1)=[O:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 131711537HCID 131711537, compoundHCID 131711544HCID 131711544, compound

Product 1

HCID 131711543HCID 131711543, compoundYield 84.7%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.774 g of diphenylmethyl α-(3ξ-carboxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate dissolved in a mixture of 18 ml of benzene and 0.1 ml of N,N-dimethylformamide is added 0.43 ml of oxalyl chloride, and the mixture stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The residue (diphenylmethyl α-(3ξ-chlorocarbonyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate) is dissolved in 10 ml of methylene chloride and mixed with 15 ml of ether solution of diazomethane, which has been prepared from 1.5 g of nitrosomethylurea, under ice-cooling, and the mixture stirred for 30 minutes. To the resulting solution of diphenylmethyl α-(3ξ-diazoacetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate is is added an ether solution of hydrogen chloride until the spot of diazoketone disappears, and the mixture concentrated under reduced pressure. The residue is purified by chromatography on 40 g of silica gel containing 10% water and eluted with benzene containing 10% ethyl acetate to yield 1.59 g of diphenylmethyl α-(3ξ-chloroacetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 84.7% yield.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue (diphenylmethyl α-(3ξ-chlorocarbonyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate) is dissolved in 10 ml of methylene chloride
  3. additionmixed with 15 ml of ether solution of diazomethane, which
  4. customhas been prepared from 1.5 g of nitrosomethylurea, under ice-
  5. temperaturecooling
  6. stirringthe mixture stirred for 30 minutes
  7. concentrationthe mixture concentrated under reduced pressure
  8. customThe residue is purified by chromatography on 40 g of silica gel containing 10% water
  9. washeluted with benzene containing 10% ethyl acetate

Sources & evidence

ORD record
ord-880a11b5abe648069fe361edcc58e2ea
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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