Diisopropyl Ether → Trifluoroacetate

HRID 414423Notes

Reaction equation

HRID 414423 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:62])[CH:24]([NH:25][C:26](=[O:61])[C:27]([C:36]4[N:37]=[C:38]([NH:41]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:39][CH:40]=4)=[CH:28][C:29]([O:31]C(C)(C)C)=[O:30])[C@H:21]3[S:20][CH2:19][C:18]=2[CH2:63][S:64][C:65]2[S:66][C:67]([CH3:70])=[N:68][N:69]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.[F:71][C:72]([F:77])([F:76])[C:73]([O-:75])=[O:74].C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[NH2:41][C:38]1[S:39][CH:40]=[C:36]([C:27](=[CH:28][C:29]([OH:31])=[O:30])[C:26]([NH:25][CH:24]2[C:23](=[O:62])[N:22]3[C:17]([C:15]([OH:16])=[O:14])=[C:18]([CH2:63][S:64][C:65]4[S:66][C:67]([CH3:70])=[N:68][N:69]=4)[CH2:19][S:20][C@H:21]23)=[O:61])[N:37]=1.[F:71][C:72]([F:77])([F:76])[C:73]([O-:75])=[O:74]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 84468TrifluoroacetateHCID 131715798HCID 131715798, compound

Product 2

HCID 84468TrifluoroacetateHCID 131715797HCID 131715797, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

7-[2-(2-tritylaminothiazol-4-yl)-2-t-butoxycarbonylmethylene-acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid diphenylmethylester (Z-isomer) (60 mg) was dissolved in anisole (0.5 ml), and the resultant solution was ice-cooled. The cooled solution was admixed with trifluoroacetate acid (2 ml), and the admixture obtained was stirred for 4 hours at 0° to 5° C. The resulting reaction solution was poured into isopropylether (50 ml), to precipitate the titled compound. The precipitate was removed by filtration to give 7-[2-(2-aminothiazol-4-yl)-2-carboxymethylene-acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (Z-isomer) trifluoroacetate (20 mg) as powder.

Workup

  1. temperaturecooled
  2. customthe admixture obtained
  3. customThe resulting reaction solution
  4. customto precipitate the titled compound
  5. customThe precipitate was removed by filtration

Sources & evidence

ORD record
ord-30c7bbb3d9ec4a76b2b3a5287ce849f8
Source dataset
uspto-grants-1988_12
Patent number
US04791197

Reaction notes

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