Acetic Acid → Diphenylmethyl 7-Amino-3-(3-chloro-1-propen-1-yl)-3-cephem-4-carboxylate

HRID 580209Notes

Reaction equation

C(=[N:8][CH:9]1[C:36](=[O:37])[N:11]2[C:12]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:13]([CH:16]=[CH:17][CH2:18][Cl:19])[CH2:14][S:15][C@H:10]12)C1C=CC=CC=1.C(O)(=O)C>C(OCC)(=O)C.CO>[NH2:8][CH:9]1[C:36](=[O:37])[N:11]2[C:12]([C:20]([O:22][CH:23]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])=[C:13]([CH:16]=[CH:17][CH2:18][Cl:19])[CH2:14][S:15][C@H:10]12

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of XVII from Preparation No. 7 (180 mg, 0.34 mmole) in ethyl acetate (10 ml) was added to a solution of Girard Reagent T [(carboxymethyl)trimethylammonium chloride hydrazide] (251 mg, 1.5 mmole) in CH3OH (10 ml) containing acetic acid (0.25 ml), at 5° C. After stirring for 30 minutes at 5° C., the mixture was concentrated to remove the CH3OH and then ethyl acetate (20 ml) was added. The ethyl acetate solution was washed with H2O (2×5 ml), saturated aqueous NaHCO3 (5 ml) and brine (5 ml), successively and dried over MgSO4. Evaporation of the solvent gave 145 mg (97%) of the title compound XVIII (Z isomer) as a yellow powder. M.p. >100° C. (dec.).

Workup

customat 5° C
concentrationthe mixture was concentrated
customto remove the CH3OH
additionethyl acetate (20 ml) was added
washThe ethyl acetate solution was washed with H2O (2×5 ml), saturated aqueous NaHCO3 (5 ml) and brine (5 ml)
dry with materialsuccessively and dried over MgSO4
customEvaporation of the solvent

Sources & evidence

ORD record: ord-7871c89c32b24331894cbff69c747f0a
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751295

Reaction notes

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