Trifluoroacetic acid → HCID 131713437, compound

HRID 1903774Notes

Reaction equation

HRID 1903774 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][C:11]([Cl:41])=[C:12]([C:14](=[N:31][O:32][CH2:33][C:34]([O:36]C(C)(C)C)=[O:35])[C:15]([NH:17][CH:18]2[C:29](=[O:30])[N:20]3[C:21]([C:26]([OH:28])=[O:27])=[C:22]([CH3:25])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:10][C:11]([Cl:41])=[C:12]([C:14](=[N:31][O:32][CH2:33][C:34]([OH:36])=[O:35])[C:15]([NH:17][CH:18]2[C:29](=[O:30])[N:20]3[C:21]([C:26]([OH:28])=[O:27])=[C:22]([CH3:25])[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713438HCID 131713438, compound

Product 1

HCID 131713437HCID 131713437, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (9.2 ml) was added to a suspension of 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer) (2.3 g) in dichloromethane (5 ml) and anisole (2.3 ml) at ambient temperature and the mixture was stirred for 1.5 hours at same temperature. To the resulting solution was added the 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 sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.2 with 10% hydrochloric acid under ice cooling. The precipitates were filtered off, washed with ice water and dried over phosphorus pentoxide in vacuo to give 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer) (1.4 g).

Workup

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

Sources & evidence

ORD record
ord-71c5941acc71469f84dc36a745588f8b
Source dataset
uspto-grants-1984_03
Patent number
US04438113

Reaction notes

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