(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → N-[2-Hydroxy-5-(1-hydroxy-2-{1-[4-(toluene-4-sulfonyl)-phenyl]-piperidin-4-ylamino}-ethyl)-phenyl]-methanesulfonamide

HRID 351711Notes

Reaction equation

HRID 351711 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:24][CH2:25][C@@H:26]([C:28]1[CH:29]=[CH:30][C:31]([OH:39])=[C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:33]=1)[OH:27]>>[OH:39][C:31]1[CH:30]=[CH:29][C:28]([CH:26]([OH:27])[CH2:25][NH:24][CH:19]2[CH2:20][CH2:21][N:16]([C:13]3[CH:12]=[CH:11][C:10]([S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:23])=[CH:2][CH:3]=4)(=[O:8])=[O:9])=[CH:15][CH:14]=3)[CH2:17][CH2:18]2)=[CH:33][C:32]=1[NH:34][S:35]([CH3:38])(=[O:37])=[O:36]

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 227133581-[4-(Toluene-4-sulfonyl)-phenyl]-piperidin-4-one

Product 1

HCID 10281140N-[2-Hydroxy-5-(1-hydroxy-2-{1-[4-(toluene-4-sulfonyl)-phenyl]-piperidin-4-ylamino}-ethyl)-phenyl]-methanesulfonamide

Procedure

The title compound was prepared according to the procedure of Example 1 from 0.13 g (0.4 mmol) of Reference Example 25, 1-[4-(Toluene-4-sulfonyl)-phenyl]-piperidin-4-one, and 0.12 g (0.5 mmol) of (R)-N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl}-methanesulfonamide, yielding 0.18 g of a white solid; m.p. 115-118° C.; MS (ES) m/z 560.0 (MH+); HRMS (FAB) Calcd. for C27H34N3O6S2 (MH+): 560.1889, Found: 560.1886.

Sources & evidence

ORD record
ord-45aab5adea28444da76aaa8b98e2677c
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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