Sodium Hydroxide → HCID 69654956, compound

HRID 1794907Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 69654864HCID 69654864, compound

Product 1

HCID 69654956HCID 69654956, compound

Procedure

The title compound was prepared from methyl 3-[(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}anilino)sulfonyl]-2-thiophenecarboxylate (which was obtained in Example 320) by NaOH hydrolysis as a pale grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.50–1.70 (m, 2 H), 1.95–2.10 (m, 2 H), 2.50–2.70 (m, 2 H), 2.95 (s, 3 H), 3.00–3.30 (m, 3 H), 3.60–3.70 (m, 2 H), 4.75–4.85 (m, 1 H), 6.10 (brs, 1 H), 6.80 (d, J=9.0 Hz, 2 H), 6.85–6.95(m, 3 H) 7.04 (d, J=5.4 Hz, 1 H), 7.08 (dd, J=8.4, 1.8 Hz, 1 H), 7.26 (d, J=1.8 Hz, 1 H), 7.39 (d, J=5.4 Hz, 1 H), 8.73 (brs, 1 H), 9.96 (brs, 1 H); MS (ES) m/z: 610.7 (MH+); HRMS Calcd. for C25H31N4O8S3 (MH+): 611.1299. Found: 611.1284.

Sources & evidence

ORD record: ord-7c44d7d7fa3f435ea1a94e71623092bc
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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