(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 69654980, compound

HRID 1794904Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([S:11](=[O:27])(=[O:26])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[NH2:29][CH2:30][C@@H:31]([C:33]1[CH:34]=[CH:35][C:36]([OH:44])=[C:37]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:38]=1)[OH:32]>>[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][CH:22]([NH:29][CH2:30][C@H:31]([OH:32])[C:33]4[CH:34]=[CH:35][C:36]([OH:44])=[C:37]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:38]=4)[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)(=[O:26])=[O:27])=[CH:9][CH:10]=1)[CH3:2]

Participants

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

HCID 69654925HCID 69654925, compound

Product 1

HCID 69654980HCID 69654980, compound

Procedure

The title compound was prepared from 4-[4-(4-oxo-piperidin-1-yl)-phenylsulfamoyl]-benzoic acid ethyl ester (which was obtained in Example 235) and N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 278 as a pale yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.40 (m, 2 H), 1.32 (t, J=7.1 Hz, 3 H), 1.75–1.90 (m, 2 H), 2.50–2.70 (m, 5 H), 2.91 (s, 3 H), 3.40–3.55 (m, 2 H), 4.32 (q, J=7.1 Hz, 2 H), 4.47 (dd, J=8.1, 4.2 Hz, 1 H), 6.70–6.90 (m, 5 H), 6.99 (dd, J=8.3, 2.0 Hz, 1 H), 7.17 (d, J=2.0 Hz, 1 H), 7.79 (d, J=8.5 Hz, 2 H), 8.07 (d, J=8.5 Hz, 2 H); MS (ES) m/z: 633.3 (MH+); HRMS Calcd. for C29H37N4O8S2 (MH+): 633.2047. Found: 633.2013.

Sources & evidence

ORD record: ord-26559781a0264097947c5e296ec78230
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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