(R)-2-Amino-5-(3-pyridyl)pentane → (S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide

HRID 2232158노트

반응식

HRID 2232158 반응식
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[C@@H:14]2[CH2:16][C:15]2([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=CC=1)([O-])=O.[CH3:34][C@@H:35]([NH2:45])[CH2:36][CH2:37][CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1>O1CCCC1>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([C:15]2([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:16][C@@H:14]2/[CH:13]=[CH:12]/[C:11]([NH:45][C@@H:35]([CH3:34])[CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[O:10])[CH:30]=[CH:29][CH:28]=1

참가 물질

4

반응물 2

HCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 70374114(S)-(E)-3-[2,2-bis(3-methoxyphenyl)cyclopropyl]-2-propenoic acid 4-nitrophenyl ester

생성물 1

HCID 86742538(S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide수율 60.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

As in example 141, (S)-(E)-3-[2,2-bis(3-methoxyphenyl)cyclopropyl]-2-propenoic acid 4-nitrophenyl ester (2.2 g) was reacted with (R)-alpha-methyl-3-pyridinebutanamine (0.81 g) in tetrahydrofuran (15 mL) at ambient temperature overnight. The crude product, isolated in the usual manner, was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to give 1.4 g of (S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide, mp 104°-106° C.

후처리

  1. customThe crude product, isolated in the usual manner
  2. customwas purified by HPLC (ethyl acetate)
  3. customcrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-52d96faf0f194649b89f0c28c0c36a3c
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04786646

반응 노트

불러오는 중…