Sodium Hydroxide → HCID 69654834, compound

HRID 1061422Notes

Reaction equation

HRID 1061422 reaction equation
[CH2:1]([N:5]([C:34]([NH:36][CH2:37][C:38]([O:40]CC)=[O:39])=[O:35])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][C@H:20]([OH:33])[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:22]=3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>>[CH2:1]([N:5]([C:34]([NH:36][CH2:37][C:38]([OH:40])=[O:39])=[O:35])[C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:13][CH2:14][CH:15]([NH:18][CH2:19][C@H:20]([OH:33])[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:22]=3)[CH2:16][CH2:17]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86584577HCID 86584577, compound

Product 1

HCID 69654834HCID 69654834, compound

Procedure

The title compound was prepared from ethyl {[(butyl-4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}anilino)carbonyl]amino}acetate (which was obtained in Example 379) by NaOH hydrolysis as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.83 (t, J=7.1 Hz, 3H), 1.15-1.60 (m, 6H), 1.85-2.00 (m, 2H), 2.65-2.95 (m, 5H), 2.92 (s, 3H), 3.42 (d, J=4.0 Hz, 2H), 3.45-3.55 (m, 2H), 3.65-3.80 (m, 2H), 4.65-4.75 (m, 1H), 5.16 (t, J=4.0 Hz, 1H), 6.83 (d, J=8.3 Hz, 1H), 6.95-7.15 (m, 5H), 7.20 (d, J=2.0 Hz, 1H); MS (ES) m/z: 576.3 (M−H)−; HRMS Calcd. for C27H38N5O7S(M−H)−: 576.2497. Found: 576.2502.

Sources & evidence

ORD record
ord-ae416069d5464a1e961b360a3fe33c32
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…