Potassium Hydroxide → HCID 86592887, compound

HRID 984487Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([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])=[C:14]([Cl:33])[C:13]=3[Cl:34])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[K+].[OH-].[Na+]>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([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])=[C:14]([Cl:33])[C:13]=3[Cl:34])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 14797Potassium Hydroxide

HCID 14798Sodium Hydroxide

HCID 86592888HCID 86592888, compound

Product 1

HCID 86592887HCID 86592887, 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 327, and KOH with NaOH, providing a white solid. 1H NMR (CDCl3, 300 MHz) δ 1.70-2.0 (m, 2H), 2.0-2.20 (m, 1H), 2.54-2.68 (m, 1H), 3.03-3.46 (m, 2H), 3.80-4.11 (m, 2H), 4.27-4.40 (m, 4H), 4.50-4.70 (m, 1H), 6.60 (d, J=8.9 Hz, 1H), 6.79 (d, J=15.3 Hz, 1H), 6.94 (d, J=8.5 Hz, 1H), 7.03 (dd, J=2.1, 8.5 Hz, 1H), 7.08 (d, J=2.1 Hz, 1H), 7.30 (d, J=8.9 Hz, 1H), 7.93 (d, J=15.3 Hz, 1H). MS (ESI+) (M−2H)− at m/z 492, 494, 496. Anal. Calcd for C23H21Cl2NO5S.0.73H2O: C, 54.43; H, 4.46; N, 2.76. Found: C, 54.43; H, 4.39; N, 2.49.

Workup

customproviding a white solid

Sources & evidence

ORD record: ord-37d9dc8f1dec4ebc858978dad7f022c0
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867203B2

Reaction notes

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