Cyclopropylmethyl carbonochloridate → HCID 53965543, compound

HRID 325463Notes

Reaction equation

HRID 325463 reaction equation
[SH:1][CH:2]1[N:5]([C:6](=[C:15]([OH:17])[CH3:16])[C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[C:4](=[O:18])[CH:3]1[NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl[C:31]([O:33][CH2:34][CH:35]1[CH2:37][CH2:36]1)=[O:32]>[Ag].C(N(CC)CC)C>[CH:35]1([CH2:34][O:33][C:31]([S:1][CH:2]2[N:5]([C:6](=[C:15]([O:17][C:31]([O:33][CH2:34][CH:35]3[CH2:37][CH2:36]3)=[O:32])[CH3:16])[C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:12])[Cl:13])=[O:8])[C:4](=[O:18])[CH:3]2[NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:32])[CH2:37][CH2:36]1

Participants

5

Reactant 2

HCID 15917591Cyclopropylmethyl carbonochloridateHCID 86735545HCID 86735545, compound

Product 1

HCID 53965543HCID 53965543, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of silver salt of 2,2,2-trichloroethyl α-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(1-hydroxyethylidene)acetate (695 mg) in hexamethyl phoshorotriamide (8 ml) is added a mixture of cyclopropylmethyl chloroformate (480 mg) and triethylamine (180 mg), and the mixture is stirred for 1 hour. The reaction mixture is poured into ice water, and is extracted with benzene. The extract solution is washed with water, dried, and evaporated in leave residue. Purification of the residue by chromatography over silica gel to give 2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(1-cyclopropylmethoxycarbonyloxyethylidene)acetate (650 mg). Yield: 64.4%.

Workup

  1. extractionis extracted with benzene
  2. washThe extract solution is washed with water
  3. customdried
  4. customevaporated in leave residue
  5. customPurification of the residue by chromatography over silica gel

Sources & evidence

ORD record
ord-9b9cca18b37e4239bc2324021beabd44
Source dataset
uspto-grants-1984_04
Patent number
US04440683

Reaction notes

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