Potassium Hydroxide → HCID 11134203, compound

HRID 984476Notes

Reaction equation

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

Participants

Reactant 3

HCID 14797Potassium Hydroxide

HCID 14798Sodium Hydroxide

HCID 70147546HCID 70147546, compound

Product 1

HCID 11134203HCID 11134203, compound

Procedure

The title compound was prepared by the procedures described in Example 155, substituting the ethyl ester from Example 137 with the ethyl ester from Example 225B, and KOH with NaOH, to give a light-yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 1.15 (d, J=6.9 Hz, 6H), 1.30-1.50 (m, 1H), 1.50-1.80 (m, 2H), 1.88-2.04 (m, 2H), 2.95-3.17 (m, 1H), 3.94-4.06 (m, 1H), 4.06-4.22 (m, 2H), 4.40-4.52 (m, 1H), 6.63 (d, J=8.7 Hz, 1H), 7.33-7.53 (m, 3H), 7.56-7.68 (m, 3H), 7.91 (dd, J=1.8, 8.4 Hz, 1H), 8.63 (d, J=8.4 Hz, 1H). MS (APCI+) (M+H)+ at m/z 455.

Workup

customto give a light-yellow solid

Sources & evidence

ORD record: ord-bc3905ce73414a558bcd0859a0a4133d
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867203B2

Reaction notes

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