Isopropanol → HCID 88179714, compound

HRID 992709Notes

Reaction equation

HRID 992709 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:50]/[O:51][CH3:52])/[C:15]([NH:17][C@@H:18]2[C:48](=[O:49])[N:20]3[C:21]([C:32]([O:34]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:33])=[C:22]([S:25][CH2:26][C:27]4[S:31][N:30]=[N:29][CH:28]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C(O)(C)C>C1(OC)C=CC=CC=1.ClCCl>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:50]/[O:51][CH3:52])/[C:15]([NH:17][C@@H:18]2[C:48](=[O:49])[N:20]3[C:21]([C:32]([OH:34])=[O:33])=[C:22]([S:25][CH2:26][C:27]4[S:31][N:30]=[N:29][CH:28]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 6422Trifluoroacetic acidHCID 88179430HCID 88179430, compound

Product 1

HCID 88179714HCID 88179714, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Under nitrogen atmosphere, trifluoroacetic acid (2.0 ml) was added dropwise to a solution of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-[(1,2,3-thiadiazol-5-yl)methylthio]-3-cephem-4-carboxylate (1.02 g) in anisole (1.0 ml) and dichloromethane (3.0 ml) under ice cooling. The mixture was stirred for 1 hour at room temperature, and then poured into 150 ml of isopropanol. The resulting precipitate was collected by filtration and treated on HP-20 (eluent: water-methanol) to afford 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-[(1,2,3-thiadiazol-5-yl)methylthio]-3-cephem-4-carboxylic acid (193.3 mg).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. additiontreated on HP-20 (eluent: water-methanol)

Sources & evidence

ORD record
ord-21c53a6c2b6c45708dc013516c9273c9
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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