Potassium Hydroxide → HCID 86759640, compound

HRID 1815501Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([O:30]CC)=[O:29])[CH2:23]4)=[O:21])=[CH:14][C:13]=3[Cl:33])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[OH-].[K+].[OH-].[Na+]>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([OH:30])=[O:29])[CH2:23]4)=[O:21])=[CH:14][C:13]=3[Cl:33])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

Reactant 3

HCID 14797Potassium Hydroxide

HCID 14798Sodium Hydroxide

HCID 86759641HCID 86759641, compound

Product 1

HCID 86759640HCID 86759640, compound

Procedure

The title compound was prepared by the procedures described in Example 155, substituting the ethyl nipecotate from Example 137 with ethyl ester from Example 283, and KOH with NaOH, to provide a white solid. 1H NMR (CDCl3, 300 MHz) δ 1.45-1.69 (m, 1H), 1.69-1.98 (m, 2H), 1.98-2.22 (m, 1H), 2.51-2.70 (m, 1H), 3.05-3.47 (m, 1H), 3.80-4.20 (m, 2H), 3.85 (s, 3H), 4.47-4.68 (m, 1H), 6.53 (d, J=3.0 Hz, 1H), 6.57 (d, J=8.1 Hz, 1H), 6.87 (d, J=15.3 Hz, 1H), 7.08 (d, J=8.1 Hz, 1H), 7.14 (d, J=3.0 Hz, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.42 (d, J=9.0 Hz, 1H), 7.51 (s, 1H), 7.52 (d, J=15.3 Hz, 1H), 7.89 (br s, 1H). MS (ESI+) (M−H+H)+ at m/z 453, 455.

Workup

customto provide a white solid

Sources & evidence

ORD record: ord-f27ecb76cfd849ccbb4003ae99a80bbf
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878700B1

Reaction notes

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