Sodium Hydroxide → HCID 10602703, compound

HRID 1061326Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 10816992HCID 10816992, compound

Product 1

HCID 10602703HCID 10602703, compound

Procedure

The title compound was prepared from (2S)-2-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-piperidine-1-yl}-benzoylamino)-3-methyl-butyric acid ethyl ester (which was obtained in Example 202) by sodium hydroxide hydrolysis as a pale yellowish solid; mp >135° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 0.90 (d, J=2.3 Hz, 3H), 0.92 (d, J=2.3 Hz, 3H), 1.45-1.55 (m, 2H), 1.90-2.05 (m, 2H), 2.05-2.20 (m, 1H), 2.60-2.94 (m, 5H), 2.94 (s, 3H), 3.70-3.85 (m, 2H), 4.11 (t, J=6.0 Hz, 1H), 4.65-4.75 (m, 1H), 6.86 (d, J=8.3 Hz, 1H), 6.91 (d, J=8.9 Hz, 2H), 7.06 (dd, J=8.3, 2.0 Hz, 1H), 7.22 (d, J=2.0 Hz, 1H), 7.65-7.75 (m, 3H); MS (ES) m/z: 549.3 (MH+); HRMS Calcd. for C26H35N4O7S (M−H)−: 547.2231. Found: 547.2229.

Sources & evidence

ORD record: ord-b85a9137158a4c37a270d665fcaddf57
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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