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

반응식

HRID 615797 반응식
[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

참가 물질

7

반응물 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

생성물 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-carboxylate수율 100.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226428Ether acetate용매

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-a46b1601d1794ddeadfbebab7cb5a24b
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04500526

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