Potassium Hydroxide → HCID 11755267, compound

HRID 984490Notes

Reaction equation

HRID 984490 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][CH:25]([C:28]([O:30]CC)=[O:29])[CH2:24][CH2:23]4)=[O:21])=[C:14]([Cl:33])[C:13]=3[Cl:34])=[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[CH2:23][CH2:24][CH:25]([C:28]([OH:30])=[O:29])[CH2:26][CH2:27]4)=[O:21])=[C:14]([Cl:33])[C:13]=3[Cl:34])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 86592892HCID 86592892, compound

Product 1

HCID 11755267HCID 11755267, compound

Procedure

The title compound was prepared by the procedures described in Example 155, substituting the ethyl ester from Example 137 with ethyl ester from Example 339, and KOH with NaOH, to give a white solid. 1H NMR (d6-DMSO, 300 MHz) δ 1.31-1.53 (m, 2H), 1.62-1.76 (m, 2H), 1.94-2.09 (m, 1H), 2.88 (brt, J=10.5 Hz, 1H), 3.13 (brt, J=10.5 Hz, 1H), 3.86 (s, 3H), 3.93 (br d, J=13.2 Hz, 1H), 4.09 (br d, J=13.2 Hz, 1H), 6.41 (d, J=8.7 Hz, 1H), 6.53 (dd, J=0.9, 3.0 Hz, 1H), 7.04 (d, J=15.3 Hz, 1H), 7.32 (dd, J=2.1, 8.7 Hz, 1H), 7.48 (d, J=3.0 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.69 (d, J=15.3 Hz, 1H), 7.73 (d, J=8.7 Hz, 1H), 7.88 (d, J=2.1 Hz, 1H). MS (ESI+) (M+H) at m/z 489, 491, 493. Anal. Calcd for C24H21Cl2N2NaO3S.0H2O: C, 56.37; H, 4.14; N, 5.48. Found: C, 56.44; H, 4.38; N, 5.20.

Workup

  1. customto give a white solid

Sources & evidence

ORD record
ord-244b51040aa24fed9f8cb9b630e9367e
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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