Diisopropyl Ether → HCID 131714494, compound

HRID 1284589Notes

Reaction equation

HRID 1284589 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:27]1[N:28]=[C:29]([NH:32][P:33]([O:37]C)([O:35]C)=[O:34])[S:30][CH:31]=1)[C:5]([NH:7][CH:8]1[C:25](=[O:26])[N:10]2[C:11]([C:22]([O-:24])=[O:23])=[C:12]([CH2:15][N+:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][S:14][C@H:9]12)=[O:6].C[Si](Br)(C)C.C(OC(C)C)(C)C>>[CH3:1][O:2][N:3]=[C:4]([C:27]1[N:28]=[C:29]([NH:32][P:33]([OH:37])([OH:35])=[O:34])[S:30][CH:31]=1)[C:5]([NH:7][CH:8]1[C:25](=[O:26])[N:10]2[C:11]([C:22]([O-:24])=[O:23])=[C:12]([CH2:15][N+:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 76113BromotrimethylsilaneHCID 131714496HCID 131714496, compound

Product 1

HCID 131714494HCID 131714494, compound

Procedure

To the mixture containing 7-[2-methoxyimino-2-(2-dimethoxyphosphorylaminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) was dropped trimethylsilyl bromide (14.80 g) at 3° to 8° C. under stirring, which was continued for 2.5 hours at ambient temperature. The reaction mixture was poured into diisopropyl ether (1.5 l) and the resultant resinous oil was separated by decantation. The oil was dissolved in water (300 ml), adjusted to pH 1 with 1N hydrochloric acid and subjected to column chromatography on a nonionic adsorption resin "Diaion HP-20" (320 ml). After the column was washed with water (1.4 l), the elution was carried out with 20% aqueous methanol. The fractions containing the object compound were collected, evaporated to remove methanol and lyophilized to give 7-[2-methoxyimino-2-(2-phosphonoaminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.3 g), mp. 155° to 164° C. (dec.).

Workup

  1. customthe resultant resinous oil was separated by decantation
  2. dissolutionThe oil was dissolved in water (300 ml)
  3. washAfter the column was washed with water (1.4 l)
  4. washthe elution
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. customevaporated
  8. customto remove methanol

Sources & evidence

ORD record
ord-361f51f04e4b4f2daf683b0b8528721d
Source dataset
uspto-grants-1986_01
Patent number
US04563449

Reaction notes

Loading…