4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → HCID 69654589, compound

HRID 1061370Notes

Reaction equation

HRID 1061370 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:28][CH2:29][C@H:30]([OH:40])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>>[OH:40][C@H:30]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[CH2:29][NH:28][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenolHCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 69654589HCID 69654589, compound

Procedure

The title compound was prepared from N-{4-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and (2S)-1-amino-3-(4-hydroxy-phenoxy)-propan-2-ol (which was obtained in Example 5) according to the procedure of Example 255 as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.65 (m, 2H), 1.95-2.15 (m, 2H), 2.06 (s, 3H), 2.50-3.20 (m, 5H), 3.55-3.70 (m, 2H), 3.80-3.90 (m, 1H), 4.05-4.20 (m, 1H), 5.70 (brs, 1H), 6.67 (d, J=9.0 Hz, 2H), 6.76 (d, J=9.0 Hz, 2H), 6.78 (d, J=9.0 Hz, 2H), 6.88 (d, J=9.0 Hz, 2H), 7.58 (d, J=9.0 Hz, 2H), 7.69 (d, J=9.0 Hz, 2H), 8.97 (s, 1H), 10.37 (s, 1H); MS (ES) m/z: 555.1 (MH+); HRMS Calcd. for C28H35N4O6S(MH+): 555.2277. Found: 555.2267.

Sources & evidence

ORD record
ord-5486008def824bf592fb243d365ac269
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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