1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → benzyl {(5S)-5-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-5-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}carbamate

HRID 659712

反応式

HRID 659712 の反応式
FC(F)(F)[C:3]([O-:5])=[O:4].F[C:9](F)(F)[C:10]([O-:12])=O.[NH3+:15][C@H:16]([C:32]1[NH:33][C:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:35][NH+:36]=1)[CH2:17][CH2:18][CH2:19][CH2:20][NH:21]C(OCC1C=CC=CC=1)=O.[CH3:47]CN=C=NCCCN(C)C.[CH:58]1[CH:59]=[CH:60][C:61]2N(O)N=N[C:62]=2[CH:63]=1.[CH3:68][O:69][C:70]1[CH:71]=[C:72]2[C:76](=[CH:77][CH:78]=1)[NH:75][C:74]([CH3:79])=[C:73]2CC(O)=O.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:68][O:69][C:70]1[CH:71]=[C:72]2[C:76](=[CH:77][CH:78]=1)[NH:75][C:74]([CH3:79])=[C:73]2[CH2:9][C:10]([NH:15][C@H:16]([C:32]1[NH:33][C:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:35][N:36]=1)[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:3](=[O:4])[O:5][CH2:47][C:62]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:63]=1)=[O:12]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 81531DiisopropylethylamineHCID 866315362-((1S)-1-ammonio-5-{[(benzyloxy)carbonyl]amino}pentyl)-5-(2-naphthyl)-1H-imidazol-3-ium bis(trifluoroacetate)

生成物 1

HCID 86631539benzyl {(5S)-5-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-5-[5-(2-naphthyl)-1H-imidazol-2-yl]pentyl}carbamate収率 77%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution (0.5 M) of the product from step 2 in DMF were added EDCI (1.5 eq.), HOBt (1.5 eq.), (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1.5 eq.) and DIPEA (6 eq.) and the reaction mixture was stirred at RT for 16 h. Then, it was diluted with EtOAc and washed with 1N HCl, brine and dried. Evaporation of the solvent under reduced pressure gave a crude that was purified by flash chromatography on silica gel (1:4 to 1:3 EtOAc/petroleum ether) to yield (77%) the title compound as a solid.

後処理

  1. washwashed with 1N HCl, brine
  2. customdried
  3. customEvaporation of the solvent under reduced pressure
  4. customgave a crude that
  5. customwas purified by flash chromatography on silica gel (1:4 to 1:3 EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-a6fd1f79528546ada0afbdf313119303
出典データセット
uspto-grants-2011_12
特許番号
US08080573B2

関連ノート

読み込み中…