Phosphorus oxychloride → HCID 131712353, compound

HRID 745429Notes

Reaction equation

HRID 745429 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:18][CH:17]=2)[C:10](O)=[O:11])[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:36][CH:37]1[C:47](=[O:48])[N:39]2[C:40]([C:44]([OH:46])=[O:45])=[CH:41][CH2:42][S:43][C@H:38]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])=[CH:20][CH:21]=2)[C:10]([NH:36][CH:37]2[C:47](=[O:48])[N:39]3[C:40]([C:44]([OH:46])=[O:45])=[CH:41][CH2:42][S:43][C@H:38]23)=[O:11])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 541218162-(2-Formamidothiazol-4-yl)-2-(4-tert-butoxycarbonylaminomethylbenzyloxyimino)acetic acid

Product 1

HCID 131712353HCID 131712353, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Formamidothiazol-4-yl)-2-(4-tert-butoxycarbonylaminomethylbenzyloxyimino)acetic acid (syn isomer, 1.4 g.), N,N-dimethylformamide (0.29 g.), phosphoryl chloride (0.6 g.), 7-amino-3-cephem-4-carboxylic acid (0.65 g.), trimethylsilylacetamide (2.5 g.) and ethyl acetate (18 ml.) were treated in a similar manner to that of Example 11-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(4-tert-butoxycarbonylaminomethylbenzyloxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.4 g.).

Sources & evidence

ORD record
ord-9b46e846881e4d76aeb5666025dbb348
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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