Sodium Hydroxide → [(4-{4-[((2R)-2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl)amino]-1-piperidinyl}benzoyl)amino]acetic acid

HRID 1061322Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 10626150Ethyl[(4-{4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}benzoyl)amino]acetate

Product 1

HCID 10553602[(4-{4-[((2R)-2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl)amino]-1-piperidinyl}benzoyl)amino]acetic acid

Procedure

The title compound was prepared from ethyl [(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}benzoyl)amino]acetate (which was obtained in Example 196) by sodium hydroxide hydrolysis as a white solid; mp >85° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.75-1.90 (m, 2H), 2.55-2.90 (m, 5H), 2.80 (s, 3H), 3.49 (d, J=4.5 Hz, 2H), 3.70-3.80 (m, 2H), 4.43 (dd, J=7.9, 4.4 Hz, 1H), 6.70 (d, J=7.4 Hz, 1H), 6.81 (dd, J=7.4, 2.0 Hz, 1H), 6.92 (d, J=8.9 Hz, 2H), 7.12 (d, J=2.0 Hz, 1H), 7.54 (t, J=4.5 Hz, 1H), 7.64 (d, J=8.9 Hz, 2H); MS (ES) m/z: 507.2 (MH+); HRMS Calcd. for C23H31N4O7S(MH+): 507.1908. Found: 507.1912.

Sources & evidence

ORD record: ord-0dfdaa588e3147be8ca6221913984acd
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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