(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → Methyl[(4-{4-[((2r)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}benzoyl)amino]acetate

HRID 1794835Notes

Reaction equation

HRID 1794835 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[CH:20][C:11]([C:12]([NH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:22][CH2:23][C@@H:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=1)[OH:25]>>[CH3:19][O:18][C:16](=[O:17])[CH2:15][NH:14][C:12](=[O:13])[C:11]1[CH:20]=[CH:21][C:8]([N:5]2[CH2:6][CH2:7][CH:2]([NH:22][CH2:23][C@H:24]([OH:25])[C:26]3[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=3)[CH2:3][CH2:4]2)=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 86584566Methyl {[4-(4-oxo-1-piperidineyl)benzoyl]amino}acetate

Product 1

HCID 91418973Methyl[(4-{4-[((2r)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}benzoyl)amino]acetate

Procedure

The title compound was prepared from methyl {[4-(4-oxo-1-piperidinyl)benzoyl]amino}acetate (which was obtained in Example 162) 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 180 as a white solid; mp>75° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.35 (m, 2 H), 1.75–1.90 (m, 2 H), 2.50–2.90 (m, 5 H), 2.91 (s, 3 H), 3.63 (s, 3 H), 3.70–3.85 (m, 2 H), 3.95(d, J=5.7 Hz, 2 H), 4.49 (dd, J=8.0, 4.3 Hz, 1 H), 6.81 (d, J=8.2 Hz, 1 H), 6.96(d, J=8.9 Hz, 2 H), 7.00 (dd, J=8.2, 2.0 Hz, 1 H), 7.17 (d, J=2.0 Hz, 1 H), 7.71 (d, J=8.9 Hz, 2 H), 8.60 (t, J=5.8 Hz, 1 H); MS (ES) m/z: 521.3 (MH+); HRMS Calcd. for C25H37N4O7S (M+): 520.2064. Found: 520.2054.

Sources & evidence

ORD record
ord-365671f1bf2a4e9cb34cdac37ae3482a
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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