3-Amino-2,2-dimethylpropanamide → 2,2-dimethyl-3-((3-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)propyl)-amino)propanamide

HRID 1499309

반응식

C[N:2](C)[CH2:3][C:4]([CH3:37])([CH3:36])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:35]=[CH:34][C:14]([CH2:15][C:16]2[CH:17]=[C:18]([C@H:23]3[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@H:26]([OH:31])[C@@H:25]([S:32][CH3:33])[O:24]3)[CH:19]=[CH:20][C:21]=2[CH3:22])=[CH:13][CH:12]=1.NCC(C)(C)C(N)=[O:43]>>[CH3:36][C:4]([CH3:37])([CH2:5][NH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]2[CH:17]=[C:18]([C@H:23]3[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@H:26]([OH:31])[C@@H:25]([S:32][CH3:33])[O:24]3)[CH:19]=[CH:20][C:21]=2[CH3:22])=[CH:34][CH:35]=1)[C:3]([NH2:2])=[O:43]

참가 물질

반응물 2

HCID 111593153-Amino-2,2-dimethylpropanamide

HCID 90183140(2S,3R,4R,5S,6R)-2-(3-(4-(3-((3-(dimethylamino)-2,2-dimethylpropyl)amino) propoxy)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol

생성물 1

HCID 760708982,2-dimethyl-3-((3-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)propyl)-amino)propanamide

실험 절차

The same procedure was employed as for amine 50, using 3-amino-2,2-dimethylpropanamide, to provide the product 51. The material was purified by prep HPLC (C18 30×100 mm column, 5-60% CH3CN/10 mM aqueous ammonium formate, 45 mL/min) and lyophilized to give the formate salt the product as a white solid. 1H NMR (400 MHz, MeOH-d4) δ ppm 7.11-7.21 (m, 3 H), 7.06 (d, J=8.1 Hz, 2 H), 6.88 (m, J=8.3 Hz, 2 H), 4.39 (d, J=9.3 Hz, 1H), 4.05-4.16 (m, 3 H), 3.94 (s, 2 H), 3.35-3.53 (m, 3 H), 3.23 (t, J=6.9 Hz, 2 H), 3.07 (s, 2 H), 2.20 (s, 3 H), 2.16-2.24 (m, 2 H), 2.14 (s, 3 H), 1.33 (s, 6 H); MS (ES+) [M+H]+=533.

출처 및 근거

ORD 기록: ord-e9f5a797525f47e0ae14c9a6c8568a5f
출처 데이터셋: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09200025B2

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