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 615804ノート

反応式

HRID 615804 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].[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

参加物

6

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

生成物 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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide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-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%.

後処理

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

出典と根拠

ORDレコード
ord-b766a768090c4ca7ae020efe3b01d63c
出典データセット
uspto-grants-1985_02
特許番号
US04500526

反応ノート

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