Phosphorus oxychloride → HCID 178453488, compound

HRID 1759663Notes

Reaction equation

HRID 1759663 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:15][O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:12]([OH:14])=O)[N:10]=1)=[O:4].P(Cl)(Cl)(Cl)=O.[NH2:29][CH:30]1[C:58](=[O:59])[N:32]2[C:33]([C:55]([OH:57])=[O:56])=[C:34]([CH:37]([S:49][C:50]3[NH:54][N:53]=[N:52][N:51]=3)[CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:35][S:36][C@H:31]12.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CC(C)=O.O.CN(C)C=O>[F:22][C:2]([F:1])([F:23])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:15][O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:12]([NH:29][CH:30]2[C:58](=[O:59])[N:32]3[C:33]([C:55]([OH:57])=[O:56])=[C:34]([CH:37]([S:49][C:50]4[NH:51][N:52]=[N:53][N:54]=4)[CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:43])[CH2:35][S:36][C@H:31]23)=[O:14])[N:10]=1)=[O:4]

Participants

9

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 54035027HCID 54035027, compoundHCID 178453487HCID 178453487, compound

Product 1

HCID 178453488HCID 178453488, compoundYield 76.2%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[2-(2,2,2-Trifluoroacetamido)thiazol-4-yl]-2-cyclopentyloxyiminoacetic acid (syn isomer, 1.5 g.), dry N, N-dimethylformamide (0.4 g.), phosphoryl chloride (0.8 g.), 7-amino-3-[1-(3-tert-butoxycarbonylaminopropyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (2.0 g.), sodium bicarbonate (1.4 g.), water (12.0 ml.), acetone (12.0 g.), and dry ethyl acetate (0.4 g.) were treated in a similar manner to that of Example 11-(1) to give 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-cyclopentyloxyiminoacetamido]-3-[1-(3-tert-butoxycarbonylaminopropyl)-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid (syn isomer, 2.60 g.).

Sources & evidence

ORD record
ord-b8c509bc2220425d8bb2d7e597d87bd1
Source dataset
uspto-grants-1982_07
Patent number
US04341775

Reaction notes

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