Reaction #55553

ord-ea89828c3ba04d619ff93379ac9743e3

Reaction equation

NC1C(=O)N2C(C(=O)O)=C(C(CCO)Sc3nnn[nH]3)CS[C@H]12
7-amino-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid
C[Si](C)(C)CC(N)=O
trimethylsilylacetamide
C#CCON=C(C(=O)O)c1csc(NC=O)n1
2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetic acid
O=P(Cl)(Cl)Cl
phosphoryl chloride
→
C#CCON=C(C(=O)NC1C(=O)N2C(C(=O)O)=C(C(CCO)Sc3nnn[nH]3)CS[C@H]12)c1csc(NC=O)n1
7-[2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid
Yield 60.4%

Reactants

NC1C(=O)N2C(C(=O)O)=C(C(CCO)Sc3nnn[nH]3)CS[C@H]12
7-amino-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid
C[Si](C)(C)CC(N)=O
trimethylsilylacetamide
C#CCON=C(C(=O)O)c1csc(NC=O)n1
2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetic acid
O=P(Cl)(Cl)Cl
phosphoryl chloride

Reagents

None

Solvents

CCOC(C)=O
ethyl acetate
CCOC(C)=O
ethyl acetate
CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

A solution of 7-amino-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (2.0 g) and trimethylsilylacetamide (5.9 g) in dry ethyl acetate (40.0 ml) and a solution of 2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetic acid (syn isomer, 1.6 g), dry dimethylformamide (0.5 g) and phosphoryl chloride (1.0 g) in dry ethyl acetate (52.0 ml) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-propargyloxyiminoacetamido]-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 2.00 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04220761uspto-grants-1980_09