(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 ethyl ester

HRID 351709Notes

Reaction equation

HRID 351709 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([CH2:23][CH2:24][CH2:25][CH3:26])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].[NH2:28][CH2:29][C@@H:30]([C:32]1[CH:33]=[CH:34][C:35]([OH:43])=[C:36]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:37]=1)[OH:31]>>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([CH2:23][CH2:24][CH2:25][CH3:26])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:17][CH2:18][CH:19]([NH:28][CH2:29][C@H:30]([OH:31])[C:32]3[CH:33]=[CH:34][C:35]([OH:43])=[C:36]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:37]=3)[CH2:20][CH2:21]2)=[CH:12][CH:11]=1)(=[O:8])=[O:9])[CH3:2]

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 69899530{Butyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino}-acetic acid ethyl ester

Product 1

HCID 69900453[Butyl-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzenesulfonyl)-amino]-acetic acid ethyl ester

Procedure

The title compound was prepared according to the procedure of Example 1 from 1.03 g (2.6 mmol) of Reference Example 43, {butyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino}-acetic acid ethyl ester, and 0.77 g (3.1 mmol) of (R)-N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl}-methanesulfonamide, yielding 1.05 g of a light yellow solid; m.p. 94-95° C.; MS (ES) m/z 627.2 (MH+); HRMS (ES) Calcd. for C28H43N4O8S2 (MH+): 627.2517, Found: 627.2505.

Sources & evidence

ORD record
ord-e2ead0a1b7f443cd9f92adcad48cc5b9
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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