Trifluoroacetic acid → HCID 178508510, compound

HRID 1194165Notes

Reaction equation

HRID 1194165 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C1(OC)C=CC=CC=1.C([NH:35][C:36]1[S:37][CH:38]=[C:39](/[C:41](=[N:69]/[O:70][CH2:71][C:72]([O:74]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:73])/[C:42]([NH:44][C@@H:45]2[C:67](=[O:68])[N:47]3[C:48]([C:55]([O:57]CC4C=CC(OC)=CC=4)=[S:56])=[C:49]([CH2:52][CH2:53][OH:54])[CH2:50][S:51][C@H:46]23)=[O:43])[N:40]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(OCC)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:35][C:36]1[S:37][CH:38]=[C:39](/[C:41](=[N:69]/[O:70][CH2:71][C:72]([OH:74])=[O:73])/[C:42]([NH:44][C@@H:45]2[C:67](=[O:68])[N:47]3[C:48]([C:55]([OH:57])=[S:56])=[C:49]([CH2:52][CH2:53][OH:54])[CH2:50][S:51][C@H:46]23)=[O:43])[N:40]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 141552859HCID 141552859, compound

Product 1

HCID 178508510HCID 178508510, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(d-2) To a mixture of trifluoroacetic acid (4 ml) and anisole (0.8 ml) was added under ice-cooling 360 mg (0.349 mM) of p-methoxybenzyl 7β-{α-(2-tritylaminothiazole-4-yl)-α-[(Z)-benzhydryloxycarbonylmethoxyimino]acetamido}-3-(2-hydroxy)ethylthio-3-cephem-4-carboxylate, and the mixture was stirred for one hour. The reaction mixture was added slowly dropwise to a mixture of diethyl ether and petroleum ether (1:2, 50 ml), thecrystals which formed were collected by filtration to give 188 mg of 7β-{α-(2-aminothiazole-4-yl)-α-[(Z)-carboxymethoxyimino]acetamido}-3-(2-hydroxy)ethylthio-3-cephem-4-carboxylic acid trifluoroacetate. The crystals and 77 mg (0.917 mM) of sodium bicarbonate were dissolved in 5 ml of water, and the solution was applied to a Sephadex HL-20 column chromatography (eluent: water) to give 164 mg of 7β-{α-(2-aminothiazole-4-yl)-α-[(Z)-carboxymethoxyimino]acetamido}-3-2-hydroxy)ethylthio-3-cephem-4-carboxylic acid sodium salt.

Workup

  1. additionwas added under ice-
  2. customthecrystals which formed
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-75f069f4cbb148c0a6dae8cf830b2995
Source dataset
uspto-grants-1989_03
Patent number
US04812562

Reaction notes

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