HCID 14460365, compound → HCID 14460366, compound

HRID 1031046Notes

Reaction equation

CC(C)([O-])C.[K+].[N:7]([CH2:10][C:11]([CH3:35])([CH3:34])[C:12](=[O:33])[CH:13]([N:27]1[CH:30](Cl)[CH2:29][C:28]1=[O:32])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])=[N+:8]=[N-:9]>C(O)(C)(C)C.O1CCCC1.C(OCC)(=O)C>[N:7]([CH2:10][C:11]([C:12]1[O:33][CH:30]2[N:27]([C:28](=[O:32])[CH2:29]2)[C:13]=1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])([CH3:35])[CH3:34])=[N+:8]=[N-:9]

Participants

Conditions

Temperature: -30 °C

Procedure

313 μl of a 0.75 M solution of potassium tert-butoxide in tert-butanol are added at -30° C. to a solution of 107 mg (0.23 mmol) of p-nitrobenzyl 5-azido-2-(4-chloro-2-oxo-1-azetidinyl)-4,4-dimethyl-3-oxopentanoate in 4.5 ml of dry tetrahydrofuran and the solution is stirred at -30° C. during the course of 30 minutes. The reaction mixture is then diluted with 20 ml of ethyl acetate, and the mixture is washed with 10 ml of water and 10 ml of NaCl solution. The aqueous phases are extracted using 10 ml of ethyl acetate and the combined organic phases are dried over MgSO4, filtered and then evaporated in vacuo. In this way, 105 mg of a yellow residue are obtained which is crystallized from methylene chloride/ diisopropyl ether. Yield 61 mg of melting point 81°-82° C. IR spectrum in CH2 --Cl2 : 2950, 2860, 2110, 1810, 1720, 1590, 1530, 1370, 1320, 1085, 1020 cm-1.

Workup

washthe mixture is washed with 10 ml of water and 10 ml of NaCl solution
extractionThe aqueous phases are extracted
dry with materialthe combined organic phases are dried over MgSO4
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-2a871b0d80c94ba781e6712e67b6391d
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108747

Reaction notes

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