Cephaloglycin → HCID 70548445, compound

HRID 372595Notes

Reaction equation

HRID 372595 reaction equation
CC(O[CH2:5][C:6]1[CH2:25][S:24][C@@H:9]2[C@H:10]([NH:13][C:14]([C@H:16]([NH2:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:26]([OH:28])=[O:27])=O.[CH2:29]([N:31]1[C:36](=[O:37])[C:35](=[O:38])[NH:34][N:33]=[C:32]1[SH:39])[CH3:30]>>[NH2:23][C@H:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:14]([NH:13][C@@H:10]1[C:11](=[O:12])[N:8]2[C:7]([C:26]([OH:28])=[O:27])=[C:6]([CH2:5][S:39][C:32]3[N:31]([CH2:29][CH3:30])[C:36](=[O:37])[C:35](=[O:38])[NH:34][N:33]=3)[CH2:25][S:24][C@H:9]12)=[O:15]

Participants

3

Reactant 2

HCID 19150CephaloglycinHCID 178462990HCID 178462990, compound

Product 1

HCID 70548445HCID 70548445, compound

Procedure

In a manner analogous to that described in Example 1 8.1 g of cephaloglycine and 3.78 g of 1,4,5,6-tetrahydro-4-ethyl-5,6-dioxo-3-mercapto-as-triazine were reacted to yield 4.19 g (40.5%); of (7R)-7-[(R)-2-amino-2-phenylacetamido]-3-[[(1,4,5,6-tetrahydro-4-ethyl-5,6-dioxo-as-triazin-3-yl)-thio]methyl]-3-cephem-4-carboxylic acid which was isolated as a Zwitter ion; yield 4.19g (40.5% melting point >180° (decomposition); [α]D20 = -86.3) (c = 0.276 in dimethylformamide).

Workup

  1. customwere reacted
  2. customto yield 4.19 g (40.5%)

Sources & evidence

ORD record
ord-a75f1dcbfa144250b4fa7d09a1298c50
Source dataset
uspto-grants-1978_05
Patent number
US04091211

Reaction notes

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