Hydrochloric Acid → HCID 88760778, compound

HRID 2287192Notes

Reaction equation

HRID 2287192 reaction equation
[C:1]([CH:4]1[O:10][CH:9]2[CH:6]([C:7](=[O:25])[N:8]2[C:11](=[C:22]([CH3:24])[CH3:23])[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[N:5]1[C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(O)=[O:2].C(Cl)(=O)[C:35]([Cl:37])=O.[N+](=CC(C1OC2C(C(=O)N2C(=C(C)C)C(OCC2C=CC=CC=2)=O)N1C(=O)C1C=CC=CC=1)=O)=[N-].Cl>C1C=CC=CC=1.CN(C)C=O.CCOCC>[Cl:37][CH2:35][C:1]([CH:4]1[O:10][CH:9]2[CH:6]([C:7](=[O:25])[N:8]2[C:11](=[C:22]([CH3:23])[CH3:24])[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[N:5]1[C:26](=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 70561159HCID 70561159, compoundHCID 131711548HCID 131711548, compound

Product 1

HCID 88760778HCID 88760778, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.8 g of benzyl α-(3ξ-carboxy-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate dissolved in a mixture of 70 ml of benzene and 0.14 ml of N,N-dimethylformamide is added 1.33 ml of oxalyl chloride at room temperature under nitrogen atmosphere, and the mixture allowed to stand for 30 minutes, and concentrated to 1/2 volume. The resulting solution of benzyl α-(3ξ-chlorocarbonyl-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylidene-acetate is mixed under ice-cooling with an ether solution of diazomethane prepared from 4 g of N-nitrosomethylurea. The resulting solution of benzyl α-(3ξ-diazoacetyl-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate is mixed with 2.1 ml of ether containing 0.47 g of hydrogen chloride at 0° C., and after 2 hours, evaporated to yield 6.3 g of benzyl α-(3ξ-chloroacetyl-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo-[3.2.0]heptan-6-yl)-α-isopropylideneacetate as an yellow-brown oil.

Workup

  1. concentrationconcentrated to 1/2 volume
  2. additionThe resulting solution of benzyl α-(3ξ-chlorocarbonyl-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylidene-acetate is mixed under ice-
  3. temperaturecooling with an ether solution of diazomethane
  4. customprepared from 4 g of N-nitrosomethylurea
  5. waitafter 2 hours
  6. customevaporated

Sources & evidence

ORD record
ord-e115f41d869946518ddc8fe88fecca93
Source dataset
uspto-grants-1981_05
Patent number
US04269773

Reaction notes

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