Morpholine → HCID 70636414, compound

HRID 1414675Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][C:13]([NH:15][CH:16]1[C:33](=[O:34])[N:18]2[CH:19]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:20]([N:23]=[C:24]=[O:25])=[CH:21][S:22][C@H:17]12)=[O:14]>>[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH2:12][C:13]([NH:15][CH:16]1[C:33](=[O:34])[N:18]2[C:19]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[C:20]([NH:23][C:24]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:25])[CH2:21][S:22][C@H:17]12)=[O:14]

Participants

Reactant 2

HCID 8083Morpholine

HCID 88819973HCID 88819973, compound

Product 1

HCID 70636414HCID 70636414, compound

Procedure

Benzhydryl 7-phenylacetamido-3-isocyanato-2-cephem-4-carboxylate reacts with 2 equivalents of isopropylamine in tetrahydrofuran at 0° for approximately 1 hour to provide benzhydryl 7-phenylacetamido-3-isopropylureido-3-cephem-4-carboxylate. Likewise morpholine reacts under similar conditions with tert-butyl 7-(2-thienylacetamido)-3-isocyanato-2-cephem-4-carboxylate to provide tert-butyl 7 -(2-thienylacetamido)-3-morpholinocarbonylamino-3-cephem-4-carboxylate. When 4'-methoxybenzyl 7-(tert-butoxycarbonylamino)-3-isocyanato-2-cephem-4carboxylate is reacted with 2.5 equivalents of N-methylaniline in methylene chloride at 0° for about 1 hour, the product isolated, after chromatography, is 4'-methoxybenzyl 7-(tert-butoxycarbonylamino)-3-(N-methyl-N-phenylureido)-3-cephem-4-carboxylate.

Sources & evidence

ORD record: ord-94cc665aaaab472d91704e298c5764d5
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04001226

Reaction notes

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