Sodium Chloride → HCID 88686710, compound

HRID 1249428Notes

Reaction equation

C(OC([NH:8][CH:9]1[C:35](=[O:36])[N:11]2[C:12]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:13](/[CH:16]=[CH:17]/[Cl:18])[CH2:14][S:15][C@H:10]12)=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[NH2:8][CH:9]1[C:35](=[O:36])[N:11]2[C:12]([C:19]([O:21][CH:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:13](/[CH:16]=[CH:17]/[Cl:18])[CH2:14][S:15][C@H:10]12

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of benzhydryl 7-t-butoxycarbonylamino-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (5.0 g) in acetonitrile (50 ml) was added p-toluenesulfonic acid monohydrate (3.23 g). After stirring at 35° C. for 50 minutes, the mixture was poured into a saturated aqueous solution of sodium chloride, adjusted to pH 7.5 with 5% aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue as triturated with n-hexane to give benzhydryl 7-amino-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (2.50 g)

Workup

extractionextracted with ethyl acetate
washThe extract was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue as triturated with n-hexane

Sources & evidence

ORD record: ord-bdeb5ce95f4a4866b533149ae992c212
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04631274

Reaction notes

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