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

반응식

HRID 659712 반응식
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]

참가 물질

8

반응물 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)

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a6fd1f79528546ada0afbdf313119303
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080573B2

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