Trifluoroacetic acid → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[2-(methylcarbamoylamino)-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 615797ノート

反応式

HRID 615797 の反応式
[CH3:1][O:2]/[N:3]=[C:4](/[C:35]1[N:36]=[C:37]([NH:40]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:38][CH:39]=1)\[C:5]([NH:7][CH:8]1[C:33](=[O:34])[N:10]2[C:11]([C:17]([O:19]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:18])=[C:12]([CH2:15]I)[CH2:13][S:14][C@H:9]12)=[O:6].[CH3:60][NH:61][C:62](=[O:73])[NH:63][C:64]1[S:65][C:66]2[CH:71]=[CH:70][N:69]=[CH:68][C:67]=2[N:72]=1.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>CN(C=O)C.CCOCC.C([O-])(=O)C>[NH2:40][C:37]1[S:38][CH:39]=[C:35](/[C:4](=[N:3]/[O:2][CH3:1])/[C:5]([NH:7][CH:8]2[C:33](=[O:34])[N:10]3[C:11]([C:17]([O-:19])=[O:18])=[C:12]([CH2:15][N+:69]4[CH:70]=[CH:71][C:66]5[S:65][C:64]([NH:63][C:62]([NH:61][CH3:60])=[O:73])=[N:72][C:67]=5[CH:68]=4)[CH2:13][S:14][C@H:9]23)=[O:6])[N:36]=1

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13239634benzhydryl (6R)-3-(iodomethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 155935472-(3-Methylureido)thiazolo[4,5-c]pyridine

生成物 1

HCID 177740057(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[2-(methylcarbamoylamino)-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate収率 100.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226428Ether acetate溶媒

実験手順

A mixture of diphenylmethyl 7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIa] (466 mg, 0.5 mmole) and 2-(3-methylureido)-thiazolo[4,5-c]pyridine (104 mg, 0.5 mmole) in 3 ml of dry DMF was stirred at room temperature for 1 hour and diluted with ether acetate to give 430 mg of crude quaternary salt, which was treated with TFA and anisole at room temperature for 30 minutes. The mixture was evaporated and triturated with ether to give 302 mg of crude Ir which was purified on a column of HP-20 resin (40 ml) using 30% CH3OH as an eluant to give 169 mg (56%) of Ir. Mp. 184°~200° C. (dec.). Estimated purity by HPLC: 40%.

後処理

  1. customto give 430 mg of crude quaternary salt, which
  2. customThe mixture was evaporated
  3. customtriturated with ether

出典と根拠

ORDレコード
ord-a46b1601d1794ddeadfbebab7cb5a24b
出典データセット
uspto-grants-1985_02
特許番号
US04500526

反応ノート

読み込み中…