Veratric Acid → (S)-2-{[(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-(3,4-dimethoxy-benzoyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid

HRID 708752노트

반응식

HRID 708752 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.CCN=C=NCCCN(C)C.Cl.C[O:27][C:28](=[O:79])[C@@H:29]([NH:46][C:47]([C@@H:49]1[CH2:58][C:57]2[CH:56]=[C:55]3[O:59][CH2:60][C@H:61]([C:63]4[CH:68]=[CH:67][C:66]([O:69][CH2:70][C:71]5[CH:76]=[CH:75][C:74]([Cl:77])=[C:73]([Cl:78])[CH:72]=5)=[CH:65][CH:64]=4)[O:62][C:54]3=[CH:53][C:52]=2[CH2:51][NH:50]1)=[O:48])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][N:41]=[C:40]([CH3:44])[C:39]=2[CH3:45])=[CH:33][CH:32]=1>C(Cl)Cl>[Cl:78][C:73]1[CH:72]=[C:71]([CH:76]=[CH:75][C:74]=1[Cl:77])[CH2:70][O:69][C:66]1[CH:67]=[CH:68][C:63]([C@H:61]2[CH2:60][O:59][C:55]3=[CH:56][C:57]4[CH2:58][C@@H:49]([C:47]([NH:46][C@@H:29]([CH2:30][C:31]5[CH:36]=[CH:35][C:34]([O:37][C:38]6[CH:43]=[CH:42][N:41]=[C:40]([CH3:44])[C:39]=6[CH3:45])=[CH:33][CH:32]=5)[C:28]([OH:79])=[O:27])=[O:48])[N:50]([C:6](=[O:8])[C:5]5[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=5)[CH2:51][C:52]=4[CH:53]=[C:54]3[O:62]2)=[CH:64][CH:65]=1

참가 물질

5

반응물 3

HCID 7121Veratric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58327121(S)-2-({(3S,8S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

생성물 1

HCID 58327502(S)-2-{[(3S,8S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-7-(3,4-dimethoxy-benzoyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3,4-Dimethoxybenzoic acid (1 eq.) was stirred in dry DCM with 0.5 eq EDCl at RT for 1 h. (S)-2-({(3S,8S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester in dry DCM (10 eq benzoic acid relative to amine) was added and the resulting mixture stirred 16 h, then directly purified by flash chromatography. The resulting compound was hydrolyzed according to General Procedure B to give the title compound (5 mg). LCMS (m/z) 919.

후처리

  1. additionwas added
  2. customdirectly purified by flash chromatography

출처 및 근거

ORD 기록
ord-87ed151041914e81939cc5242a7d4663
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175003B2

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