HCID 178508102, compound → HCID 178502853, compound

HRID 918258Notes

Reaction equation

HRID 918258 reaction equation
NC1C(=O)N2C([C:16](O)=[O:17])=C(CSC3NN=NC=3)CS[C@H]12.[CH:21]1[C:26]([C@@H:27]([NH2:50])[C:28]([NH:30][C@@H:31]2[C:34](=[O:35])[N:33]3[C:36]([C:47]([OH:49])=[O:48])=[C:37]([CH2:40][S:41][C:42]4[N:46]=[N:45][NH:44][CH:43]=4)[CH2:38][S:39][C@H:32]23)=[O:29])=[CH:25][CH:24]=[C:23]([OH:51])[CH:22]=1>C(Cl)Cl>[CH:25]1[C:26]([C@@H:27]([NH2:50])[C:28]([NH:30][C@@H:31]2[C:34](=[O:35])[N:33]3[C:36]([C:47]([OH:49])=[O:48])=[C:37]([CH2:40][S:41][C:42]4[N:46]=[N:45][NH:44][CH:43]=4)[CH2:38][S:39][C@H:32]23)=[O:29])=[CH:21][CH:22]=[C:23]([OH:51])[CH:24]=1.[CH3:16][OH:17]

Participants

4

Reactant 2

HCID 178508102HCID 178508102, compoundHCID 178511839HCID 178511839, compound

Product 1

HCID 178502853HCID 178502853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acylation of 7-amino-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (7-TACA) to BL-S640 has been carried out in methylene chloride with D-(-)-p-hydroxyphenylglycyl chloride hydrochloride. The yield to BL-S640 methanol solvate was about 45% on a biopotency basis. There was about 15% activity in the mother liquor and about 25% insoluble solids which is unreacted 7-TACA and 7-TACA decomposition product with degraded β-lactam.

Sources & evidence

ORD record
ord-7256554a3c554d8e81bf79fe1c1f02f0
Source dataset
uspto-grants-1976_07
Patent number
US03970651

Reaction notes

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