Methanethiol → HCID 14460308, compound

HRID 2371899Notes

Reaction equation

CS.OC[CH2:5][S:6]([CH:9]1[NH:12][C:11](=[O:13])[CH:10]1[CH:14]([O:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])[CH3:15])(=O)=O>C(#N)C.O.C(Cl)Cl>[CH3:5][S:6][CH:9]1[NH:12][C:11](=[O:13])[CH:10]1[CH:14]([O:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=1)=[O:18])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

1.17 g (16.7 mmol) of the Na salt of methyl mercaptan are added 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 at 0° C., and the mixture is stirred at 0° C. for 20 minutes. The reaction mixture is diluted with 100 ml of methylene chloride and 25 ml of H2O, and, after separating off the organic phase, the aqueous phase is extracted three times with 25 ml of methylene chloride in each case. The combined organic phases are dried over MgSO4, filtered and the solvent is removed in vacuo, to give 3.80 g of the title compound 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=7 Hz, J=2 Hz), 4.70 (d, J=2 Hz, 1 H), 5.12 (m, 1 H), 5.20 (s, 2 H), 6.45 (broad s, 1 H), 7.50 (d, J=8.5 Hz, 2 H), 8.20 (d, J=8.5 Hz, 2 H).

Workup

customafter separating off the organic phase
extractionthe aqueous phase is extracted three times with 25 ml of methylene chloride in each case
dry with materialThe combined organic phases are dried over MgSO4
filtrationfiltered
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-bcc8d89485684fc6adf1536d02c2ab95
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05096899

Reaction notes

Loading…