Propylene Oxide → HCID 21413118, compound

HRID 436036Notes

Reaction equation

HRID 436036 reaction equation
[CH2:1]([O:5][C:6]([CH:8]([N:12]1[CH:15]([S:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[CH:14]([NH:28][C:29](=[O:38])[CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:13]1=[O:39])[C:9]([CH3:11])=[CH2:10])=[O:7])[CH2:2][CH2:3][CH3:4].[Br:40]N1C(C)(C)C(=O)N(Br)C1=O.C1OC1C>[Hg].ClCCCl>[CH2:1]([O:5][C:6]([CH:8]([N:12]1[CH:15]([S:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])[CH:14]([NH:28][C:29](=[O:38])[CH2:30][O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:13]1=[O:39])[C:9]([CH2:11][Br:40])=[CH2:10])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6378Propylene OxideHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 21413138HCID 21413138, compound

Product 1

HCID 21413118HCID 21413118, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2.7 g (5 mmoles) of 1-(1-n-butyloxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one, 200 ml of 1,2-dichloroethane, 1,4 g (5 mmoles ) of 1,3-dibromo-5,5-dimethylhydantoin and 3 ml of propylene oxide was irradiated under nitrogen for 3 hours at 14° C with a Hanovia TQ 150 mercury high pressure lamp using a Pyrex filter. After concentrating the reaction mixture, the residue was chromatographed over silica gel [toluene -ethyl acetate 5:1 (v/v)] to obtain 300 mg (0.5 mmole) of 1-(1-n-butyloxycarbonyl-2-bromomethylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one.

Workup

  1. filtrationfilter
  2. concentrationAfter concentrating the reaction mixture
  3. customthe residue was chromatographed over silica gel [toluene -ethyl acetate 5:1 (v/v)]

Sources & evidence

ORD record
ord-bc273ff5d9324d11bb88ec4c7b89d81f
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

Loading…