Trifluoroacetic acid → HCID 131713548, compound

HRID 1262769Notes

Reaction equation

HRID 1262769 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:39][O:40][CH2:41][C:42]([O:44]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:43])[C:15]([NH:17][CH:18]2[C:37](=[O:38])[N:20]3[C:21]([C:26]([O:28][CH2:29][O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[S:27])=[C:22]([CH3:25])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>ClCCl>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:39][O:40][CH2:41][C:42]([OH:44])=[O:43])[C:15]([NH:17][CH:18]2[C:37](=[O:38])[N:20]3[C:21]([C:26]([O:28][CH2:29][O:30][C:31](=[O:36])[C:32]([CH3:33])([CH3:34])[CH3:35])=[S:27])=[C:22]([CH3:25])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131713549HCID 131713549, compound

Product 1

HCID 131713548HCID 131713548, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.7 g) was added to a solution of pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (3.1 g) in dichloromethane (12.4 ml) and anisole (0.9 g) with ice-cooling and the mixture was stirred for an hour at ambient temperature. To the resulting solution was added isopropyl ether and stirred. The precipitates were collected by filtration, washed with isopropyl ether. The precipitates were added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with saturated aqueous potassium carbonate. The separated aqueous layer was adjusted to pH 2.5 with 10% hydrochloric acid. The precipitates were filtrated off, washed with water and dried over phosphorus pentoxide in vacuo to give pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (1.69 g).

Workup

  1. temperaturecooling
  2. stirringstirred
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with isopropyl ether
  5. additionThe precipitates were added to a mixture of ethyl acetate and water
  6. filtrationThe precipitates were filtrated off
  7. washwashed with water
  8. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-570b88f8941f4147af3f4969a78819a4
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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