Phosphorus oxychloride → HCID 88690597, compound

HRID 894817Notes

Reaction equation

HRID 894817 reaction equation
[NH2:1][CH:2]1[C:22](=[O:23])[N:4]2[C:5]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)=[O:10])=[CH:6][CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.[F:32][C:33]([F:57])([F:56])[C:34]([NH:36][C:37]1[S:38][CH:39]=[C:40]([C:42](=NOCC2C=CC(C)=CC=2)[C:43](O)=[O:44])[N:41]=1)=[O:35].P(Cl)(Cl)(Cl)=O>O1CCCC1.CN(C)C=O>[F:57][C:33]([F:32])([F:56])[C:34]([NH:36][C:37]1[S:38][CH:39]=[C:40]([CH2:42][C:43]([NH:1][CH:2]2[C:22](=[O:23])[N:4]3[C:5]([C:9]([O:11][CH2:12][C:13]4[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=4)=[O:10])=[CH:6][CH2:7][S:8][C@H:3]23)=[O:44])[N:41]=1)=[O:35]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 54293344HCID 54293344, compound

Product 1

HCID 88690597HCID 88690597, compoundYield 129.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (2.01 g.), trimethylsilylacetamide (5.51 g.) and tetrahydrofuran (40 ml.) and a solution of 2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-methylbenzyloxyimino)acetic acid (syn isomer, 2.32 g.), phosphoryl chloride (1.20 g.) and N,N-dimethylformamide (570 mg.) in tetrahydrofuran (12 ml.) were treated in a similar manner to that of Example 1-(1) to give 4-nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-acetamido]-3-cephem-4-carboxylate (syn isomer, 4.43 g.).

Sources & evidence

ORD record
ord-3cfbe113ccc84326bbed307b0db76545
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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