Potassium Hydroxide → HCID 9806603, compound

HRID 1861688Notes

Reaction equation

HRID 1861688 reaction equation
C([O:3][C:4](=[O:37])[CH:5]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:36])[C:28]2[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:35])=[CH:22][CH:21]=1)[C:6]([NH:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])=[O:7])C.[OH-].[K+]>CCO.C1COCC1.O>[Cl:34][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:35])[C:28]=1[C:27]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH:5]([C:6]([NH:8][C:9]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[O:7])[C:4]([OH:37])=[O:3])=[CH:21][CH:22]=1)=[O:36]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 18621256HCID 18621256, compound

Product 1

HCID 9806603HCID 9806603, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 5 (0.59 g, 1.1 mmol) in EtOH (5 ml), THF (2 ml) and water (2 ml) was treated with KOH (1M aqueous solution, 1.62 ml, 1.62 mmol) and the reaction stirred for 2.5 h. The mixture was concentrated in vacuo and acidified to pH1 with 10% hydrochloric acid, to give a white precipitate which was isolated by filtration and washed with water, triturated with boiling MeOH and washed with Et2O to give the title compound as a white solid (300 mg, 54%). δH (DMSO d6) 10.65 (1H, s, NH), 9.04 (1H, s, NH), 7.6-7.46 (5H, m, Ar—H), 7.28-7.16 (3H, m, Ar—H), 6.65 (2H, d, J 8.4 Hz, Ar—H), 3.74 (1H, m, CHCH2), 3.68 (6H, s, OMe), 3.30 (1H, m, CHCHAHB) and 3.06 (1H, m, CHCHAHB). m/z (ESI, 60V) 517, 519 (MH+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a white precipitate which
  3. customwas isolated by filtration
  4. washwashed with water
  5. customtriturated with boiling MeOH
  6. washwashed with Et2O

Sources & evidence

ORD record
ord-cb8f446d22a94f3fa5907e451273b83e
Source dataset
uspto-grants-2003_03
Patent number
US06534513B1

Reaction notes

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