Trifluoroacetic acid → HCID 71311, compound

HRID 1904649Notes

Reaction equation

HRID 1904649 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:28]1[N:29]=[C:30]([NH:33]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:31][CH:32]=1)[C:5]([NH:7][CH:8]1[C:26](=[O:27])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[S:21][CH:20]=[N:19][C:18]=3[CH3:22])[CH2:13][S:14][C@H:9]12)=[O:6].FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)[C:5]([NH:7][CH:8]1[C:26](=[O:27])[N:10]2[C:11]([C:23]([OH:25])=[O:24])=[C:12]([CH:15]=[CH:16][C:17]3[S:21][CH:20]=[N:19][C:18]=3[CH3:22])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131715962HCID 131715962, compound

Product 1

HCID 71311HCID 71311, compound

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-[2-Methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer) pivaloyloxymethyl ester (0.160 g) was dissolved in anisole (0.5 ml). The resultant solution was admixed with trifluoroacetic acid (1.15 ml) under ice-cooling, followed by stirring for 30 minutes again under ice-cooling. The reaction solution was mixed with isopropyl ether (30 ml), and the powder substance deposited was recovered by filtration and washed with isopropyl ether. The solid obtained was dissolved in ethyl acetate (20 ml), washed with ice-coole aqueous saturated sodium hydrogen carbonate solution (10 ml). The organic phase was separated from the aqueous phase, dried over anhydrous sodium sulfate and concentrated 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) pivaloyloxymethyl ester (0.083 ) was thus obtained.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationthe powder substance deposited was recovered by filtration
  4. washwashed with isopropyl ether
  5. customThe solid obtained
  6. washwashed with ice-coole aqueous saturated sodium hydrogen carbonate solution (10 ml)
  7. customThe organic phase was separated from the aqueous phase
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58ad59b538d545f183e82aa56bb083fa
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

Loading…