Dimethylformamide → HCID 131712509, compound

HRID 848389Notes

Reaction equation

HRID 848389 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.CN(C)C=O.[NH2:30][CH:31]1[C:41](=[O:42])[N:33]2[C:34]([C:38]([OH:40])=[O:39])=[CH:35][CH2:36][S:37][C@H:32]12>CC(C)=O.O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:10]([NH:30][CH:31]2[C:41](=[O:42])[N:33]3[C:34]([C:38]([OH:40])=[O:39])=[CH:35][CH2:36][S:37][C@H:32]23)=[O:12])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 54077075HCID 54077075, compound

Product 1

HCID 131712509HCID 131712509, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-formamidothiazol-4-yl)-2-cyclopentyloxyiminoacetic acid (syn isomer, 1.5 g.), phosphoryl chloride (974 mg.), N,N-dimethylformamide (464 mg.) and tetrahydrofuran (15 ml.) and a solution of 7-amino-3-cephem-4-carboxylic acid (1.38 g.) in 50% aqueous acetone (14 ml.) were treated in a similar manner to that of Example 15-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.75 g.).

Sources & evidence

ORD record
ord-908157d5f4814009a76a9e3e5f0a1bb8
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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