HCID 14460307, compound → HCID 14460308, compound

HRID 1031047Notes

Reaction equation

OC[CH2:3][S:4]([CH:7]1[NH:10][C:9](=[O:11])[CH:8]1[CH:12]([O:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16])[CH3:13])(=O)=O>C(#N)C.O.C(Cl)Cl>[CH3:3][S:4][CH:7]1[NH:10][C:9](=[O:11])[CH:8]1[CH:12]([O:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[O:16])[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

1.17 g (16.7 mmol) of methyl mercaptan Na salt are added at 0° C. to a solution of 4.48 g (11.1 mmol) of 4-(2-hydroxyethylsulphonyl)-3-[1-(p-nitrobenzyloxycarbonyloxy)-ethyl]-azetidin-2-one in 11 ml of acetonitrile and 11 ml of H2O and the mixture is stirred at 0° C. during the course of 20 minutes. The reaction mixture is diluted with 100 ml of methylene chloride and 25 ml of H2O and the aqueous phase is extracted three times with 25 ml each of methylene chloride after separating off the organic phase. The purified organic phases are dried over MgSo4 and filtered, and the solvent is removed in vacuo, 3.80 g of title compound being obtained as a slightly yellowish non-crystalline compound. NMR spectrum in CDCl3 : δ=1.45 (d, J=7 Hz, 3 H), 2.12 (s, 3 H), 3.3 (dd, J=Hz, J=2 Hz), 4.70 (d, J=2 Hz, 1 H), 5.12 (m, 1 H), 5.20 (s, 2 H), 6.45 (wide s, 1 H), 7.50 (d, J=8.5 Hz, 2 H), 820 (d, J=8.5 Hz, 2 H).

Workup

extractionthe aqueous phase is extracted three times with 25 ml each of methylene chloride
customafter separating off the organic phase
customThe purified organic phases are dried over MgSo4
filtrationfiltered
customthe solvent is removed in vacuo, 3.80 g of title compound
custombeing obtained as a slightly yellowish non-crystalline compound

Sources & evidence

ORD record: ord-b9da08395e7b4f2fbfb80c0e314cdd97
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108747

Reaction notes

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