Triethylamine → HCID 178521132, compound

HRID 426994Notes

Reaction equation

HRID 426994 reaction equation
[SH:1][C:2]1[N:3]=[N:4][C:5]([C:9]([OH:11])=O)=[C:6]([OH:8])[N:7]=1.C(N(CC)CC)C.S(Cl)([Cl:21])=O.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>C(Cl)Cl>[SH:1][C:2]1[N:3]=[N:4][C:5]([C:9]([Cl:21])=[O:11])=[C:6]([OH:8])[N:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 11708267BistrimethylsilylacetamidHCID 178524938HCID 178524938, compound

Product 1

HCID 178521132HCID 178521132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to that of Example 1-4), 3-mercapto-5-hydroxy-1,2,4-triazine-6-carbonyl chloride, which was prepared from 3-mercapto-5-hydroxy-1,2,4-triazine-6-carboxylic acid (1.73 g), triethylamine (1.0 g), dimethyllformamide (30 ml) and thionyl chloride (1.19 g), was treated with a mixture of 7-(D-2-phenylglycinamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (4.0 g) and bis(trimethylsilyl) acetamide (6.4 g) in methylene chloride (40 ml). Thus obtained reaction mixture was worked up in a similar manner to that of Example 1--1) to give power (870 mg) of 7-[D-2-(3-mercapto-5-hydroxy-1,2,4-triazine-6-carboxamido)-2-phenylacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, mp 175° to 179° C. (dec).

Workup

  1. customThus obtained reaction mixture

Sources & evidence

ORD record
ord-0eec236ff0364cecbf03bf29383700be
Source dataset
uspto-grants-1979_10
Patent number
US04172198

Reaction notes

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