Methanol → benzyl N-(3-methoxy-2-oxoazetidin-3-yl)carbamate

HRID 371205

Reaction equation

Cl[N:2]1[CH2:5][CH:4]([N:6](Cl)[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:3]1=[O:18].CO.C[O-].[Li+].[CH3:24][O:25]P(OC)OC>O1CCCC1.C(OCC)(=O)C.C1C=CC=CC=1.C(OCC)(=O)C.C(O)(=O)C>[CH3:24][O:25][C:4]1([NH:6][C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:5][NH:2][C:3]1=[O:18]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 730 mg (0.0025 mole) of 1-chloro-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-2-azetidinone in 5 ml of tetrahydrofuran is cooled to -78° C. and 4 ml of methanol containing 285 mg of lithium methoxide is added. After 20 minutes at -78° C., 0.6 ml of acetic acid and 0.6 ml of trimethylphosphite are added. The solution is stirred for 5 minutes at -78° C., allowed to warm to ambient temperature and stirred for 30 minutes. The resulting solution is diluted with ethyl acetate, washed with 5% sodium bicarbonate, water, 5% potassium bisulfate, water, saturated salt solution, and dried. Solvent removal gives an oil that is applied to four 20×20 cm×1 mm silica gel plates. Development with benzene-ethyl acetate (1:1) and isolation of the major UV-active band of Rf=0.25 gives 91 mg of oil that crystallizes from ether to give a solid. Recrystallization from ether gives the title compound, melting point 112°-114° C.

Workup

temperatureto warm to ambient temperature
stirringstirred for 30 minutes
washwashed with 5% sodium bicarbonate, water, 5% potassium bisulfate, water, saturated salt solution
customdried
customSolvent removal
customgives an oil that

Sources & evidence

ORD record: ord-a7908853de714a3d9b596a866368d291
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04529698

Linked notes

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