Sodium Hydroxide → HCID 10008017, compound

HRID 1794829Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 10793544HCID 10793544, compound

Product 1

HCID 10008017HCID 10008017, compound

Procedure

The title compound was prepared from 2-(4-(4-{2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidin-1-yl}-benzoylamino)-4-methyl-pentanoic acid ethyl ester (which was obtained in Example 198) by sodium hydroxide hydrolysis as a white solid; mp>177° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 0.87 (d, J=6.3 Hz, 3 H) 0.90(d, J=6.3 Hz, 3 H), 1.35–1.75 (m, 5 H), 1.90–2.00 (m, 2 H), 2.60–2.90 (m, 5 H), 2.94 (s, 3 H), 3.65–3.80 (m, 2 H), 4.25–4.35 (m, 1 H), 4.60–4.65 (m, 1 H), 6.85 (d, J=8.3 Hz, 1 H), 6.90 (d, J=8.9 Hz, 2 H), 7.05 (dd, J=8.3, 1.9 Hz, 1 H), 7.21 (d, J=1.9 Hz, 1 H), 7.73 (d, J=8.9 Hz, 2 H), 7.98 (d, J=7.7 Hz, 1 H); MS(ES) m/z: 561.3 (M−H)−; HRMS Calcd. for C27H37N4O7S (M−H)−: 561.2377. Found: 561.2381.

Sources & evidence

ORD record: ord-7062db48601d4844a625aad460aa938a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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