Dicyclohexylcarbodiimide → tert-butyl (3S,5R)-3-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(5-methyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

HRID 2168928노트

반응식

HRID 2168928 반응식
[CH3:1][C:2]1[NH:6][N:5]=NN=1.[C:7]([O:11][C:12]([N:14]1[CH2:19][C@@H:18]([N:20]([C:25]([C:27]2[N:31]([CH2:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[C:30]3[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=3[N:28]=2)=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17][C@@H:16]([C:42](O)=[O:43])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C1CCC(N=C=NC2CCCCC2)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:37][O:36][CH2:35][CH2:34][CH2:33][CH2:32][N:31]1[C:30]2[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=2[N:28]=[C:27]1[C:25]([N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C@H:18]1[CH2:17][C@@H:16]([C:42]2[O:43][C:2]([CH3:1])=[N:6][N:5]=2)[CH2:15][N:14]([C:12]([O:11][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:13])[CH2:19]1)=[O:26]

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 58355779(3R,5S)-(tert-butoxycarbonyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acidHCID 178434708HCID 178434708, 화합물

생성물 1

HCID 58355175tert-butyl (3S,5R)-3-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(5-methyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate수율 35.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Methyltetrazole (63 mg) and (3R,5S)-1-(tert-butoxycarbonyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (265 mg) were dissolved in toluene (5 ml), DCC (155 mg) was added and the mixture was stirred at 100° C. for 12 hr. The reaction mixture was diluted with ethyl acetate, filtered and the solvent of the mother liquor was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) was concentrated under reduced pressure to give the object product (100 mg).

후처리

  1. filtrationfiltered
  2. customthe solvent of the mother liquor was evaporated under reduced pressure
  3. washa fraction eluted with ethyl acetate-hexane (1:1-1:0)
  4. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-18f3dbfda82f43c8b88c263ad9af9dfd
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045436B2

반응 노트

불러오는 중…