1,3-Diamino-2-propanol → (3R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)-N-(3-amino-2-hydroxypropyl)piperidine-1-carboxamide

HRID 253594

Reaktionsgleichung

Reaktionsgleichung von HRID 253594
[CH2:1]([C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C@:12]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26](Cl)=[O:27])[CH2:21]1)([OH:19])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH3:2].[NH2:33][CH2:34][CH:35]([OH:38])[CH2:36][NH2:37]>C(Cl)Cl>[CH2:1]([C:3]1[CH:32]=[CH:31][CH:30]=[CH:29][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C@:12]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]([NH:33][CH2:34][CH:35]([OH:38])[CH2:36][NH2:37])=[O:27])[CH2:21]1)([OH:19])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH3:2]

Komponenten

4

Edukt 2

HCID 611571,3-Diamino-2-propanolHCID 57786487(R)-3-((S)-1-(2-(2-Ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carbonyl Chloride

Produkt 1

HCID 57786506(3R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)-N-(3-amino-2-hydroxypropyl)piperidine-1-carboxamideAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxy pentyl)piperidine-1-carbonyl chloride (<0.05 mmol) in CH2Cl2, there was added excess 1,3-diaminopropan-2-ol (˜0.1 mL). The resulting solution was stirred at rt for 1 h, the CH2Cl2 was removed, and the residue was purified by prep HPLC to give (3R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)-N-(3-amino-2-hydroxypropyl)piperidine-1-carboxamide (10.0 mg, 39%) as its TFA salt. 1H NMR (400 MHz, CD3OD): 7.64 (d, 1H), 7.32 (d, 1H), 7.04-7.20 (m, 4H), 6.74 (d, 1H), 6.56 (d, 1-H), 4.40 (d, 1H), 3.82 (m, 2H), 3.26 (t, 2H), 3.24 (s, 3H), 2.96 (m, 1H), 2.78 (m, 2H), 2.62 (q, 2H), 2.40 (m, 2H), 1.94 (m, 1H), 1.22-1.64 (m, 7H), 1.08 (t, 3H), 0.98 (m, 1H); MS m/z 514 (M+H+).

Aufarbeitung

  1. customthe CH2Cl2 was removed
  2. customthe residue was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-be5bfef008bb4f5bbd19e50c85a2f680
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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