Trifluoroacetic acid → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-carboxy-[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 615804노트

반응식

HRID 615804 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].[C:60]([C:63]1[S:64][C:65]2[CH:70]=[CH:69][N:68]=[CH:67][C:66]=2[N:71]=1)([OH:62])=[O:61].C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>CS(C)=O>[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+:68]4[CH:69]=[CH:70][C:65]5[S:64][C:63]([C:60]([OH:62])=[O:61])=[N:71][C:66]=5[CH:67]=4)[CH2:13][S:14][C@H:9]23)=[O:6])[N:36]=1

참가 물질

6

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 20426418[1,3]Thiazolo[4,5-c]pyridine-2-carboxylic acid

생성물 1

HCID 177739680(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-carboxy-[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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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-carboxythiazolo[4,5-c]pyridine [prepared according to the procedure of Zhur. Obshchei Khim., 26, 613 (1956); C.A., 50, 13906 (1956)] (90 mg, 0.5 mmole) in 2 ml of DMSO was stirred at room temperature for 1.5 hours and diluted with ethyl acetate-ether to give 375 mg of crude quaternary salt, which was treated with 5 ml of TFA and 0.1 ml of anisole at room temperature for 15 minutes. The mixture was evaporated in vacuo and triturated with ether to give 213 mg of crude Iv. The crude product was dissolved into a small volume of phosphate buffer (pH 7.0) and chromatographed on a column of packing (20 ml) in PrepPAK/C18 cartridge. The column was eluted with water (200 ml) and 10% aqueous CH3OH (150 ml) to afford 51 mg (17%) of the title compound (Iv) as an amorphous powder. Mp. 144°~160° C. (dec.). Estimated purity by HPLC: 85%.

후처리

  1. customprepared
  2. customto give 375 mg of crude quaternary salt, which
  3. customThe mixture was evaporated in vacuo
  4. customtriturated with ether

출처 및 근거

ORD 기록
ord-b766a768090c4ca7ae020efe3b01d63c
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04500526

반응 노트

불러오는 중…