4-Toluenesulfonyl chloride → 3-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 467255Notes

Reaction equation

C(N(CC)CC)C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH3:20])[C:15]([OH:17])=O)[N:13]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[CH3:32][C:33]([O:35][CH2:36][C:37]1[CH2:46][S:45][C@@H:40]2[C@H:41]([NH2:44])[C:42](=[O:43])[N:39]2[C:38]=1[C:47]([OH:49])=[O:48])=[O:34]>CC(N(C)C)=O>[C:33]([O:35][CH2:36][C:37]1[CH2:46][S:45][C@@H:40]2[CH:41]([NH:44][C:15](=[O:17])[C:14]([C:12]3[N:13]=[C:9]([NH2:8])[S:10][CH:11]=3)=[N:18][O:19][CH3:20])[C:42](=[O:43])[N:39]2[C:38]=1[C:47]([OH:49])=[O:48])(=[O:34])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

The process of Example 8 was repeated except that after addition of triethylamine to the syn isomer of 2-(2-amino-4-thiazolyl)-2-methoxyimino-acetic acid, the mixture was cooled at 0° C. and the tosyl chloride in dimethylacetamide was added over 15 to 20 minutes. The reaction with 7-amino-cephalosporanic acid took place over 30 minutes.

Workup

customover 30 minutes

Sources & evidence

ORD record: ord-8af598b7fc174c279128346cca511361
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05159070

Reaction notes

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