Oxygen → HCID 22812923, compound

HRID 224548Notes

Reaction equation

[CH2:1]([O:5][C@H:6]1[N:9]([C:10](=C(C)C)[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:30])[C@@H:7]1[NH:31][C:32](=[O:40])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:2]([CH3:4])=[O:3].[O:41]=O>C(Cl)Cl>[CH2:1]([O:5][C@H:6]1[N:9]([C:10](=[O:41])[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:30])[C@@H:7]1[NH:31][C:32](=[O:40])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:2]([CH3:4])=[O:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of diphenylmethyl α-[4(R)-acetonyloxy-3(R)-phenylacetamido-2-oxo-azetidin-1-yl]-α-isopropylideneacetate (2.342 g; 4.33 mmoles) in methylene chloride (40 ml) is introduced ozonized oxygen for 25 minutes at -78° C. Excess ozone is purged with nigrogen gas, and the mixture is mixed with dimethyl sulfide (3 ml), and stirred at -78° C. for 30 minutes, and at room temperature for 30 minutes. The reaction mixture is mixed with three drops of acetic acid, washed with water, dried over sodium sulfate, and evaporated under reduced pressure to give the product.

Workup

customExcess ozone is purged with nigrogen gas
additionthe mixture is mixed with dimethyl sulfide (3 ml)
waitat room temperature for 30 minutes
additionThe reaction mixture is mixed with three drops of acetic acid
washwashed with water
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customto give the product

Sources & evidence

ORD record: ord-ad00c3afa8d844f681fa0ca1b72eea9b
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04233216

Reaction notes

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