Ethyl Acetate → 7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[3-(3-aminomethylpyridinio)-1-propen-1-yl]-3-cephem-4-carboxylate

HRID 580201ノート

反応式

HRID 580201 の反応式
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:40][O:41][CH3:42])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O:24]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:23])=[C:15]([CH:18]=[CH:19][CH2:20]I)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.C(OC([NH:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1)=O)(C)(C)C.C(OCC)(=O)C>CS(C)=O>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:40][O:41][CH3:42])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O-:24])=[O:23])=[C:15]([CH:18]=[CH:19][CH2:20][N+:54]4[CH:55]=[CH:56][CH:57]=[C:52]([CH2:51][NH2:50])[CH:53]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 13948280tert-Butyl (pyridin-3-ylmethyl)carbamateHCID 131715581Diphenylmethyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate

生成物 1

HCID 1317155927-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[3-(3-aminomethylpyridinio)-1-propen-1-yl]-3-cephem-4-carboxylate収率 1.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of diphenylmethyl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (IX-1) (E, 716 mg, 1 mmole) and 3-(t-butyloxycarbonylaminomethyl)pyridine (516 mg, 2 mmoles) in DMSO (2 ml) was stirred at ambient temperature for 30 minutes. The mixture was poured into ethyl acetate (200 ml), and the precipitate was collected by filtration, washed well with ethyl acetate and dried. A mixture of the quaternized salt (500 mg), sodium bisulfite (50 mg) in HCOOH (5 ml) was stirred at 40°-50° C. for 80 minutes and evaporated to dryness under reduced pressure. The residual solid was dissolved in water (40 ml), and the mixture was neutralized with NaHCO3. Insoluble material was filtered off, and the filtrate was chromatographed on a reverse phase column (packing of PrepPAK-500/C18 cartridge, 100 ml), eluting with water, 5%, 10%, 20% and 30% aqueous CH3OH, successively. The fractions containing the desired compound were combined, evaporated and lyophilized to provide 10 mg (1.8%) of the title compound (I-1I) (E) as a tan powder.

後処理

  1. filtrationthe precipitate was collected by filtration
  2. washwashed well with ethyl acetate
  3. customdried
  4. additionA mixture of the quaternized salt (500 mg), sodium bisulfite (50 mg) in HCOOH (5 ml)
  5. stirringwas stirred at 40°-50° C. for 80 minutes
  6. customevaporated to dryness under reduced pressure
  7. dissolutionThe residual solid was dissolved in water (40 ml)
  8. filtrationInsoluble material was filtered off
  9. customthe filtrate was chromatographed on a reverse phase column (packing of PrepPAK-500/C18 cartridge, 100 ml),
  10. washeluting with water, 5%, 10%, 20% and 30% aqueous CH3OH
  11. additionThe fractions containing the desired compound
  12. customevaporated

出典と根拠

ORDレコード
ord-03ac11a9452b4b18a85a06a9bb09888d
出典データセット
uspto-grants-1988_06
特許番号
US04751295

反応ノート

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