N,O-bis(trimethylsilyl)acetamide → Diisopropyl Ether

HRID 580219Notes

Reaction equation

[CH3:1]/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.Cl.[NH2:14][CH:15]1[C:42](=[O:43])[N:17]2[C:18]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:19](/[CH:22]=[CH:23]\[CH2:24][Cl:25])[CH2:20][S:21][C@H:16]12.Cl.[NH2:45][C:46]1[S:50][N:49]=[C:48](/[C:51](=[N:55]/[O:56][CH2:57][CH3:58])/[C:52](Cl)=[O:53])[N:47]=1>C(Cl)Cl.C(OCC)(=O)C>[CH:29]([O:28][CH:26]([CH3:18])[CH3:1])([CH3:30])[CH3:36].[NH2:45][C:46]1[S:50][N:49]=[C:48](/[C:51](=[N:55]/[O:56][CH2:57][CH3:58])/[C:52]([NH:14][CH:15]2[C:42](=[O:43])[N:17]3[C:18]([C:26]([O:28][CH:29]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:27])=[C:19]([CH:22]=[CH:23][CH2:24][Cl:25])[CH2:20][S:21][C@H:16]23)=[O:53])[N:47]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a mixture of N,O-bis(trimethylsilyl)acetamide (2.3 ml, 9 mmoles) and crystalline diphenylmethyl 7-amino-3-[3-chloro-1-(Z)-propen-1-yl]-3-cephem-4-carboxylate hydrochloride (XVIII) (1.338 g, 2.8 mmoles) (from Preparation No. 12) in methylene chloride (10 ml) was added 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-ethoxyiminoacetyl chloride hydrochloride (800 mg, 2.95 mmoles) portionwise, with stirring, at -10° C. and the mixture was allowed to stand at 0° C. for 2 hours. The mixture was diluted with ethyl acetate (200 ml), washed with water and evaporated under reduced pressure. Trituration of the residue with isopropyl ether afforded the title product VIII-2 as an amorphous powder. Yield 1.70 g (95%). Mp. >150° C. (dec.).

Workup

washwashed with water
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-24c8eb50b8e14aed8dc5595f8c64374d
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751295

Reaction notes

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