Phenylacetyl chloride → HCID 131711534, compound

HRID 2287179Notes

Reaction equation

HRID 2287179 reaction equation
[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:32])[N:9]2[C:12](=[C:29]([CH3:31])[CH3:30])[C:13]([O:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[NH:6]1)([O:3][CH3:4])=[O:2].C(N(CC)CC)C.[C:40]1([CH2:46][C:47](Cl)=[O:48])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:1]([CH:5]1[O:11][CH:10]2[C:7]([C:47](=[O:48])[CH2:46][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:8](=[O:32])[N:9]2[C:12](=[C:29]([CH3:30])[CH3:31])[C:13]([O:15][CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:14])[NH:6]1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 13019672HCID 13019672, compound

Product 1

HCID 131711534HCID 131711534, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 16.46 g of diphenylmethyl α-(3ξ-carbomethoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 160 ml of methylene chloride are added 9.6 ml of triethylamine and 9 ml of phenylacetyl chloride under ice-cooling, and the mixture stirred at room temperature for 2 hours. The reaction mixture is then washed with water, dried on magnesium sulfate and concentrated under reduced pressure. The residue is chromatographed on 200 g of silica gel containing 10% water and eluted with benzene containing 10% ethyl acetate to yield 17 to 19 g of diphenylmethyl α-(3ξ-carbomethoxy-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)α-isopropylideneacetate in 80 to 90% yield.

Workup

  1. temperaturecooling
  2. washThe reaction mixture is then washed with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on 200 g of silica gel containing 10% water
  6. washeluted with benzene containing 10% ethyl acetate

Sources & evidence

ORD record
ord-53ec6d35501942369efefada71004657
Source dataset
uspto-grants-1981_05
Patent number
US04269773

Reaction notes

Loading…