1,2-Dichloroethane → N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-N'-[(2S,3R)-1-(3,5-difluorophenyl)-4-[[1-(3-ethylphenyl)cyclopropyl]amino]-3-hydroxybutan-2-yl]butanediamide;formic acid

HRID 14332

반응식

HRID 14332 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][C@H:6]([NH:22][C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C@H:7]([OH:21])[CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH3:20])[CH:14]=2)[CH2:12][CH2:11]1.[CH2:34](Cl)[CH2:35]Cl.[CH:38]1[CH:39]=C[C:41]2[N:46](O)N=[N:44][C:42]=2[CH:43]=1>CN(C=O)C>[N:46]12[CH2:35][CH2:34][CH:43]([CH2:38][CH2:39]1)[C@H:42]([NH:44][C:26](=[O:28])[CH2:25][CH2:24][C:23]([NH:22][C@@H:6]([CH2:5][C:4]1[CH:30]=[C:31]([F:33])[CH:32]=[C:2]([F:1])[CH:3]=1)[C@H:7]([OH:21])[CH2:8][NH:9][C:10]1([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH3:20])[CH:14]=3)[CH2:12][CH2:11]1)=[O:29])[CH2:41]2.[CH:26]([OH:28])=[O:27]

참가 물질

5

반응물 3

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 575121114-[((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl)amino}-2-hydroxypropyl)amino]-4-oxobutanoic acid

생성물 1

HCID 86594206N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-N'-[(2S,3R)-1-(3,5-difluorophenyl)-4-[[1-(3-ethylphenyl)cyclopropyl]amino]-3-hydroxybutan-2-yl]butanediamide;formic acid수율 149.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
45 °C

실험 절차

To a solution of R-aminoquinuclidine (0.086 g, 0.434 mmol) TEA (0.302 ml, 2.17 mmol), and anhydrous DMF (2.5 ml) was added 4-[((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl]amino}-2-hydroxypropyl)amino]-4-oxobutanoic acid (0.200 g, 0.434 mmol), EDC (0.125 g, 0.651 mmol), and HOBT (0.088 g, 0.651 mmol) under nitrogen, with stirring at 45° C. overnight. Reaction mixture was quenched with 10% sodium bicarbonate (aq.) then extracted with ethyl acetate then concentrated in vacuo, yielding product (0.200 g). Prep-HPLC yielded the product as its formate salt. (ES+: 569.3)

후처리

  1. customReaction mixture
  2. customwas quenched with 10% sodium bicarbonate (aq.)
  3. extractionthen extracted with ethyl acetate
  4. concentrationthen concentrated in vacuo

출처 및 근거

ORD 기록
ord-2333b7cf0c3441a087984319d431d95b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

연결된 노트

불러오는 중…