Diisopropyl Ether → HCID 178436975, compound

HRID 1262771Notes

Reaction equation

HRID 1262771 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8](=[N:39][O:40][CH2:41][C:42]([O:44]C(C)(C)C)=[O:43])[C:9]([NH:11][CH:12]2[C:37](=[O:38])[N:14]3[C:15]([C:21]([O:23]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:22])=[C:16]([CH2:19][CH3:20])[CH2:17][S:18][C@H:13]23)=[O:10])[CH:5]=[CH:4][CH:3]=1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:8](=[N:39][O:40][CH2:41][C:42]([OH:44])=[O:43])[C:9]([NH:11][CH:12]2[C:37](=[O:38])[N:14]3[C:15]([C:21]([OH:23])=[S:22])=[C:16]([CH2:19][CH3:20])[CH2:17][S:18][C@H:13]23)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7914Diisopropyl EtherHCID 131713547Benzhydryl 7-[2-(6-aminopyridin-2-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate

Product 1

HCID 178436975HCID 178436975, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

The solution of benzhydryl 7-[2-(6-aminopyridin-2-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate (syn isomer, 2.3 g) in trifluoroacetic acid (10 ml) and anisole (2 ml) was stirred for 2 hours at ambient temperature. The resultant solution was poured into diisopropyl ether (300 ml) and the precipitates were collected by filtration. The precipitates were dissolved in an aqueous solution of sodium bicarbonate (pH 7.5). The aqueous solution was washed with ethyl acetate and was adjusted to pH 2.3 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(6-aminopyridin-2-yl)-2-carboxymethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylic acid (syn isomer, 0.87 g), mp. 164° to 167° C. (dec.).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. dissolutionThe precipitates were dissolved in an aqueous solution of sodium bicarbonate (pH 7.5)
  3. washThe aqueous solution was washed with ethyl acetate
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-2aa4b09c0cd9440298d46ae51ce66935
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

Loading…