(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → [Butyl-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzenesulfonyl)-amino]-acetic acid benzyl ester

HRID 351706Notes

Reaction equation

HRID 351706 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH2:17]([O:24][C:25](=[O:48])[CH2:26][N:27]([CH2:44][CH2:45][CH2:46][CH3:47])[S:28]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]2)=[CH:33][CH:32]=1)(=[O:30])=[O:29])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:24][C:25](=[O:48])[CH2:26][N:27]([CH2:44][CH2:45][CH2:46][CH3:47])[S:28]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:38][CH2:39][CH:40]([NH:1][CH2:2][C@H:3]([OH:4])[C:5]3[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=3)[CH2:41][CH2:42]2)=[CH:33][CH:32]=1)(=[O:30])=[O:29])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 69899200(Butyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino)-acetic acid benzyl ester

Product 1

HCID 10122730[Butyl-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzenesulfonyl)-amino]-acetic acid benzyl ester

Procedure

The title compound was prepared from N-[5-((1R)-2-Amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide and Reference Example 18, (butyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino)-acetic acid benzyl ester, according to the procedure of Example 1 as a white solid; mp 59-64° C.; 1H NMR (300 MHz, DMSO-d6) δ 0.78 (t, 3H), 1.10-1.40 (m, 6H), 1.80-1.95 (m, 2H), 2.60-3.00 (m, 5H), 2.91 (s, 3H), 3.05 (t, 2H), 3.70-3.80 (m, 2H), 4.04 (s, 2H), 4.40-4.50 (m, 1H), 5.20 (s, 2H), 6.80 (d, 1H), 6.95 (d, 2H), 7.00 (d, 2H), 7.18 (d, 1H), 7.30-7.45 (m, 5H), 7.50 (d, 2H); MS (ES) m/z: 689.1 (MH+).

Sources & evidence

ORD record
ord-49c8a88b11fb4f17bb1a79256d7bcc3f
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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