Triphenyl phosphite → HCID 131714070, compound

HRID 1154542Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([Cl:18])[CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[C:5]([OH:7])=O.ClCl.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH2:43][CH:44]1[C:55](=[O:56])[N:46]2[C:47]([C:52]([OH:54])=[O:53])=[C:48]([CH3:51])[CH2:49][S:50][C@H:45]12.C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C>ClCCl.CO>[CH3:1][O:2][N:3]=[C:4]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([Cl:18])[CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[C:5]([NH:43][CH:44]1[C:55](=[O:56])[N:46]2[C:47]([C:52]([OH:54])=[O:53])=[C:48]([CH3:51])[CH2:49][S:50][C@H:45]12)=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

Four hundred twenty milligrams of α-methoxyimino-α-(8-chloro-2-naphthyl)acetic acid were converted to the acid chloride by reaction with excess chlorine and 500 mg of triphenyl phosphite in 20 ml of dichloromethane. The reaction mixture was added in one portion to a stirred solution of 350 mg of 7-amino-3-methyl-3-cephem-4-carboxylic acid in 5 ml of dichloromethane containing 2 ml of bis(trimethylsilyl)trifluoroacetamide. The reaction mixture was stirred at 25° C. for six hours and then diluted by addition of 20 ml of methanol. The solvent was removed by evaporation under reduced pressure to provide 7-[α-methoxyimino-α-(8-chloro-2-naphthyl)acetamido]-3-methyl-3-cephem-4-carboxylic acid. The product thus formed is dissolved in formic acid containing zinc metal dust to give, following isolation and purification, 7-(8-chloro-2-naphthyl)glycylamido-3-methyl-3-cephem-4-carboxylic acid.

Workup

customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-839a6f8a1a11409e97f40071c2a77230
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04490370

Reaction notes

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