Phosphorus oxychloride → 7-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 648418Notes

Reaction equation

HRID 648418 reaction equation
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.[CH2:26]([O:29][N:30]=[C:31]([C:35]1[N:36]=[C:37]([NH:40][C:41](=[O:46])[C:42]([F:45])([F:44])[F:43])[S:38][CH:39]=1)[C:32](O)=[O:33])[C:27]#[CH:28].C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O>CN(C)C=O>[CH2:26]([O:29][N:30]=[C:31]([C:35]1[N:36]=[C:37]([NH:40][C:41](=[O:46])[C:42]([F:45])([F:43])[F:44])[S:38][CH:39]=1)[C:32]([NH:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:33])[C:27]#[CH:28]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 544030392-(2-Propynyloxyimino)-2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]acetic acidHCID 705155727-amino-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317124097-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acidYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Amino-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (1.93 g) and 2-(2-propynyloxyimino)-2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]acetic acid (syn isomer) (1.61 g) were reacted in the presence of Vilsmeier reagent prepared from dimethylformamide and phosphorus oxychloride to give 7-[2-(2-propynyloxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-[1-(2-carboxyethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (3.0 g).

Sources & evidence

ORD record
ord-8cc918ad1b9b4bf5b7f0159b38712aba
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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