Triethylamine → HCID 86742436, compound

HRID 622441Notes

Reaction equation

C(N(CC)CC)C.[N+:8]([C:11]1[CH:23]=[CH:22][C:14]([CH2:15][O:16][C:17](=[O:21])[C:18](Cl)=[O:19])=[CH:13][CH:12]=1)([O-:10])=[O:9].[CH3:24][Si:25]([CH3:45])([CH3:44])[O:26][C@@H:27]([C@@H:29]1[C@@H:32]([CH:33]([C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[S:36])[CH3:34])[NH:31][C:30]1=[O:43])[CH3:28]>C(Cl)Cl>[CH3:44][Si:25]([CH3:24])([CH3:45])[O:26][C@@H:27]([C@@H:29]1[C@@H:32]([CH:33]([C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[S:36])[CH3:34])[N:31]([C:18](=[O:19])[C:17]([O:16][CH2:15][C:14]2[CH:22]=[CH:23][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=2)=[O:21])[C:30]1=[O:43])[CH3:28]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 0.71 ml of triethylamine and 1.1 g of p-nitrobenzyloxyoxalyl chloride in 10 ml of methylene chloride was added to a solution of 0.9 g of (3S,4S)-3-[(1R)-1-trimethylsilyloxyethyl]-4-[(1RS)-1-(phenylthiocarbonyl)ethyl]-2-azetidinone in 10 ml of methylene chloride, cooled to about -30° C., and the mixture was stirred for 35 minutes at the same temperature. The reaction mixture was worked up and purified in the same manner as in Preparation 1(3), giving (3S,4S)-3-[(1R)-1-trimethylsilyloxyethyl]-4-[(1RS)-1-(phenylthiocarbonyl)ethyl]-1-(p-nitrobenzyloxyoxalyl)-2-azetidinone as an oil.

Workup

custompurified in the same manner as in Preparation 1(3)

Sources & evidence

ORD record: ord-6cf758bcb87b423abe6af37b44104b07
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04771046

Reaction notes

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