1-Hydroxybenzotriazole → N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycyl)amino-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

HRID 2185422ノート

反応式

HRID 2185422 の反応式
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:23]([O:27][C:28]([N:30]1[CH2:37][C@H:36]([NH:38][C:39](=[O:44])[CH2:40][N:41]([CH3:43])[CH3:42])[CH2:35][C@H:31]1[C:32]([OH:34])=O)=[O:29])([CH3:26])([CH3:25])[CH3:24].[N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[C:47]([NH:55][C:56](=[O:75])[C@@H:57]2[CH2:61][C@@H:60]([NH:62][C:63](=[O:74])[C@H:64]([OH:73])[CH2:65][CH2:66][C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[CH2:59][NH:58]2)[CH:46]=1>ClCCl.C(N(CC)CC)C>[N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[C:47]([NH:55][C:56](=[O:75])[C@@H:57]2[CH2:61][C@@H:60]([NH:62][C:63](=[O:74])[C@H:64]([OH:73])[CH2:65][CH2:66][C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[CH2:59][N:58]2[C:32](=[O:34])[C@@H:31]2[CH2:35][C@@H:36]([NH:38][C:39](=[O:44])[CH2:40][N:41]([CH3:43])[CH3:42])[CH2:37][N:30]2[C:28]([O:27][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:29])[CH:46]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21341539N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycylamino)-L-ProlineHCID 59895122trans-4-((R)-2-Hydroxy-4-Phenylbutrylamino)-L-Proline 3-Quinolylamide

生成物 1

HCID 21341541N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycyl)amino-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

Triethylamine (33 μL), 1-hydroxybenzotriazole (30 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46 mg) were added to a suspension of the crude N-tert-butoxycarbonyl-trans-4-(N,N-dimethylglycylamino)-L-proline (B) and trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (Compound D101 (H), 84 mg) in dichloromethane (5 mL) at 0° C. After stirring at 0° C. for 30 min and at room temperature for 14 hr, the solvent was removed in vacuo. The residue was diluted with saturated sodium hydrogen carbonate and extracted with chloroform-methanol (10:1,v/v). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (Whatman, PLK5F Silica Gel 150, chloroform:methanol=10:1, v/v) to afford the title compound (76 mg) as a colorless glassy solid: mass spectrum (EI+) m/e 715 (M+); (FAB+) m/e 716 (M+1).

後処理

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with saturated sodium hydrogen carbonate
  3. extractionextracted with chloroform-methanol (10:1,v/v)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography (Whatman, PLK5F Silica Gel 150, chloroform

出典と根拠

ORDレコード
ord-4370e04f32e54440a5e7e9f314e341e7
出典データセット
uspto-grants-2002_06
特許番号
US06399629B1

反応ノート

読み込み中…