Diisopropyl Ether → HCID 131713352, compound

HRID 905492Notes

Reaction equation

HRID 905492 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][C:36]([O:38]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:37])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][C:36]([OH:38])=[O:37])[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 7914Diisopropyl EtherHCID 131713353HCID 131713353, compound

Product 1

HCID 131713352HCID 131713352, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of tert-butoxycarbonylmethyl 7-[2-(2-aminothiazol-4-yl)-2-benzhydryloxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (3.0 g) in trifluoroacetic acid (10 ml) and anisole (5 ml) was stirred at 25° to 30° C. for an hour. The reaction mixture was poured into diisopropyl ether (150 ml), and the precipitates were collected by filtration and dissolved in 5% aqueous sodium bicarbonate (50 ml). The aqueous solution was washed with ethyl acetate and then adjusted to pH 2.3 with 10% hydrochloric acid. The precipitated substance was collected by filtration and washed with water to give carboxymethyl 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (1.7 g).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. dissolutiondissolved in 5% aqueous sodium bicarbonate (50 ml)
  3. washThe aqueous solution was washed with ethyl acetate
  4. filtrationThe precipitated substance was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-bdeed463cb9f44b8b4db53bb0dbaa7fc
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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