Citric Acid → HCID 131715470, compound

HRID 569141Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH:18][CH2:19][CH3:20])[C:15]([OH:17])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.[NH2:26][C@@H:27]1[C:56](=[O:57])[N:29]2[C:30]([C:40]([O:42][CH:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:31]([CH2:34][O:35][C:36](=[O:39])[NH:37][CH3:38])[CH2:32][S:33][C@H:28]12.CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH:18][CH2:19][CH3:20])[C:15]([NH:26][C@@H:27]2[C:56](=[O:57])[N:29]3[C:30]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)=[O:41])=[C:31]([CH2:34][O:35][C:36](=[O:39])[NH:37][CH3:38])[CH2:32][S:33][C@H:28]23)=[O:17])[N:13]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -65 °C

Procedure

To a solution of 2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid (1.49 g) in dichloromethane (60 ml) are added triethylamine (0.83 ml) and methanesulfonyl chloride (0.4 ml) at -65° C., and the mixture is stirred for 3 hours at -65° C. To the mixture is added diphenylmethyl 7β-amino-3-methylcarbamoyloxymethyl-3-cephem-4-carboxylate (2.26 g) and N-methylmorpholine (0.55 ml) in dichloromethane (60 ml). After 2 hours, the reaction mixture is neutralized with 10% citric acid, washed with water, dried, and concentrated to give diphenylmethyl 7β-[2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-methylcarbamoyloxymethyl-3-cephem-4-carboxylate (3.12 g). Yield: 85%.

Workup

waitAfter 2 hours
washwashed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-0e55db6dee164a04b21f59e039095628
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04731362

Reaction notes

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