(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 69655049, compound

HRID 1794836Notes

Reaction equation

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

Participants

Reactant 2

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

HCID 69654989HCID 69654989, compound

Product 1

HCID 69655049HCID 69655049, compound

Procedure

The title compound was prepared from methyl 4-methyl-2-[(2S)-4-(4-oxo-piperidin-1-yl)-benzylamino]-pentanoic acid methyl ester (which was obtained in Example 166) 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>90° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 0.86 (d, J=6.4 Hz, 3 H), 0.92 (d, J=6.4 Hz, 3 H), 1.20–1.40 (m, 2 H), 1.50–1.95 (m, 5 H), 2.55–2.92 (m, 5 H), 2.91 (s, 3 H), 3.62 (s, 3 H), 3.70–3.85 (m, 2 H), 4.40–4.55 (m, 2 H), 6.82 (d, J=8.2 Hz, 1 H), 6.93 (d, J=8.9 Hz, 2 H), 7.00 (dd, J=8.2, 2.0 Hz, 2 H), 7.18 (d, J=2.0 Hz, 1 H), 7.75 (d, J=8.9 Hz, 2 H), 8.34 (d, J=7.7 Hz, 1 H); MS (ES) m/z: 577.3 (MH+); HRMS Calcd. for C28H41N4O7S (MH+): 577.2690. Found: 577.2682.

Sources & evidence

ORD record: ord-0d510492ef614cf89686c2058435b55d
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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