Pyridine → HCID 178477371, compound

HRID 1165954Notes

Reaction equation

HRID 1165954 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[N:14]=[C:15]([NH:18][C:19](=[O:22])[CH2:20][Cl:21])[S:16][CH:17]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[C:29]1([CH:35]([O:42][C:43]([C:45]2[N:50]3[C:51](=[O:54])[C@@H:52]([NH2:53])[C@H:49]3[S:48][CH2:47][C:46]=2[CH:55]([S:57][C:58]2[NH:62][N:61]=[N:60][N:59]=2)[CH3:56])=[O:44])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N1C=CC=CC=1>C(Cl)Cl>[C:29]1([CH:35]([O:42][C:43]([C:45]2[N:50]3[C:51](=[O:54])[C@@H:52]([NH:53][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:13]4[N:14]=[C:15]([NH:18][C:19](=[O:22])[CH2:20][Cl:21])[S:16][CH:17]=4)[C@H:49]3[S:48][CH2:47][C:46]=2[CH:55]([S:57][C:58]2[NH:62][N:61]=[N:60][N:59]=2)[CH3:56])=[O:44])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 12763201alpha-t-Butyloxycarbonylamino-alpha-[2-(chloroacetamido)thiazol-4-yl)acetic acidHCID 178477368HCID 178477368, compound

Product 1

HCID 178477371HCID 178477371, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 349 mg of α-t-butyloxycarbonylamino-α-[2-(chloroacetamido)thiazol-4-yl]acetic acid in 5 ml of methylene chloride is added 249 mg of phosphorous pentachloride, and the mixture is stirred at room temperature. The mixture is added dropwise under stirring to the solution of 494 mg of 7β-amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester dissolved in 5 ml of methylene chloride, followed by the addition of 474 mg of pyridine. After that, the stirring is continued for further 1 hour at room temperature. The reaction solution is washed with 0.5N hydrochloric acid and then with water, and dried. The oily product obtained by the distillation of the solvent is purified by a column chromatography packed with silica gel. The procedure gives 513 mg of 7β-{α-t-butyloxycarbonylamino-α-[2-(chloroacetamido)thiazol-4-yl]acetamido}-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester.

Workup

  1. additionThe mixture is added dropwise
  2. washThe reaction solution is washed with 0.5N hydrochloric acid
  3. dry with materialwith water, and dried
  4. customThe oily product obtained by the distillation of the solvent
  5. customis purified by a column chromatography

Sources & evidence

ORD record
ord-d380b312595f4633a7038f1b078885af
Source dataset
uspto-grants-1990_03
Patent number
US04912212

Reaction notes

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