Trifluoroacetic acid → HCID 71311, compound

HRID 1904650Notes

Reaction equation

HRID 1904650 reaction equation
C([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:57])[CH:24]([NH:25][C:26](=[O:56])[C:27](=[N:53][O:54][CH3:55])[C:28]3[N:29]=[C:30]([NH:33]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:31][CH:32]=3)[C@H:21]2[S:20][CH2:19][C:18]=1[CH:58]=[CH:59][C:60]1[S:64][CH:63]=[N:62][C:61]=1[CH3:65])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.[F:66][C:67]([F:72])([F:71])[C:68]([OH:70])=[O:69].C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[CH3:55][O:54][N:53]=[C:27]([C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)[C:26]([NH:25][CH:24]1[C:23](=[O:57])[N:22]2[C:17]([C:15]([OH:16])=[O:14])=[C:18]([CH:58]=[CH:59][C:60]3[S:64][CH:63]=[N:62][C:61]=3[CH3:65])[CH2:19][S:20][C@H:21]12)=[O:56].[F:66][C:67]([F:72])([F:71])[C:68]([O-:70])=[O:69]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131715964HCID 131715964, compound

Product 2

HCID 71311HCID 71311, compoundHCID 84468Trifluoroacetate

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

7-[2-Methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid benzhydryl ester (0.11 g) was dissolved in anisole (0.33 mg), to which was added trifluoroacetic acid (1.1 ml) under ice-cooling. The solution so obtained was stirred for 1 hour under ice-cooling and the reaction solution was admixed with isopropyl ether (30 ml) to deposit a precipitate. The precipitate was recovered by filtration, washed with isopropyl ether and dried under reduced pressure. 7-[2-Methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer) trifluoroacetate (0.067 g) was obtained.

Workup

  1. temperaturecooling
  2. customThe solution so obtained
  3. temperaturecooling
  4. filtrationThe precipitate was recovered by filtration
  5. washwashed with isopropyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-696d21f3c292443e945a7ad7b744c2cc
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

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