Glutamic acid diethyl ester → (2S)-2-(3-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)ureido)pentanedioic acid

HRID 45681

반응식

HRID 45681 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].ClC1C=C2C(=C(Cl)C=1)CN(C)CC2C1C=CC(N)=CC=1.[NH2:41][C@@H:42]([CH2:48][CH2:49][C:50]([O:52]CC)=[O:51])[C:43]([O:45]CC)=[O:44].N[C@@H](CC(OC)=O)[C:57](OC)=[O:58]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([NH:17][C:57](=[O:58])[NH:41][C@@H:42]([CH2:48][CH2:49][C:50]([OH:52])=[O:51])[C:43]([OH:45])=[O:44])[CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 4

HCID 73961Glutamic acid diethyl esterHCID 1112071,4-Dimethyl L-aspartateHCID 98361943-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)anilineHCID 99443944-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

생성물 1

HCID 67464724(2S)-2-(3-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl)ureido)pentanedioic acid

실험 절차

Following the procedures outlined in Example 34, substituting 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline (intermediate 31.5) for 4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline and (S)-diethyl 2-aminopentanedioate for (S)-dimethyl 2-aminosuccinate gave, after purification by preparative HPLC, the title compound as a TFA salt. 1H-NMR (300 MHz, DMSO-d6, ppm): δ 8.74 (s, 1H), 7.67 (s, 1H), 7.42 (m, 1H), 7.27-7.25 (m, 2H), 6.79 (m, 2H), 6.52-6.49 (m, 1H), 4.63-4.58 (m, 1H), 4.44 (m, 2H), 4.20-4.16 (m, 1H), 3.72-3.64 (m, 2H), 2.99 (s, 3H), 2.34-2.27 (m, 2H), 2.01-1.97 (m, 2H), 1.82-1.77 (m, 2H). MS 480 [M+H]+.

후처리

  1. customgave
  2. customafter purification by preparative HPLC

출처 및 근거

ORD 기록
ord-628f5206a39b4ab080c8784e2bf705d9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541448B2

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