Trifluoromethanesulfonic anhydride → HCID 14305051、化合物

HRID 37281ノート

反応式

HRID 37281 の反応式
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][O:9][C:10]([O:12][C@@H:13]([C@H:15]2[C:21](=[O:22])[N:20]3[C@@H:16]2[CH2:17][C:18](=O)[C@@H:19]3[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[CH3:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH2:63][C:64]1[S:65][CH:66]=[C:67]([C@@H:69]2[CH2:73][C@H:72]([SH:74])[CH2:71][N:70]2[C:75]([O:77][CH2:78][C:79]2[CH:84]=[CH:83][C:82]([N+:85]([O-:87])=[O:86])=[CH:81][CH:80]=2)=[O:76])[N:68]=1>ClCCl>[NH2:63][C:64]1[S:65][CH:66]=[C:67]([C@@H:69]2[CH2:73][C@H:72]([S:74][C:18]3[CH2:17][C@H:16]4[N:20]([C:21](=[O:22])[C@@H:15]4[C@H:13]([O:12][C:10]([O:9][CH2:8][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:38][CH:37]=4)=[O:11])[CH3:14])[C:19]=3[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=3)=[O:24])[CH2:71][N:70]2[C:75]([O:77][CH2:78][C:79]2[CH:84]=[CH:83][C:82]([N+:85]([O-:87])=[O:86])=[CH:81][CH:80]=2)=[O:76])[N:68]=1

参加物

6

反応物 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 143050474-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylateHCID 18638803(2S,4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 14305051HCID 14305051、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1- (4-nitrobenzyloxycarbonyloxy)ethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (1.92 g) in dichloromethane (50 ml) were added N,N-diisopropyl-N-ethylamine (0.76 ml) and trifluoromethanesulfonic anhydride (0.73 ml) at -30° C., and the solution was stirred at the same temperature for 30 minutes. To this solution was added (2S, 4S)-2-(2-aminothiazol-4-yl)-4-mercapto-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (1.13 g) in dichloromethane (20 ml) at -30° C. and the solution was stirred at 0° C. for 3 hours. The mixture was washed in turn with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed on silica gel (60 g) eluting with a mixture of dichloromethane and acetone (5:1 V/V) to give 4-nitrobenzyl (5R,6S)-3-[(2S,4S)-2-(2-aminothiazol-4-yl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-(4-nitrobenzyloxycarbonyloxy) ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.85 g).

後処理

  1. stirringthe solution was stirred at 0° C. for 3 hours
  2. washThe mixture was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe oily residue was chromatographed on silica gel (60 g)
  6. washeluting with a mixture of dichloromethane and acetone (5:1 V/V)

出典と根拠

ORDレコード
ord-b5b4ba9cdfb041fbaf9dd7d8316c63f4
出典データセット
uspto-grants-1995_05
特許番号
US05420122

反応ノート

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