Potassium Hydroxide → HCID 178524144, compound

HRID 574680Notes

Reaction equation

HRID 574680 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]([NH:10][C:11]2[C:12]([OH:27])=[N:13][C:14]([C:17]3[CH:21]=[C:20]([C:22]([O:24]CC)=[O:23])[O:19][N:18]=3)=[N:15][CH:16]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>O>[C:28]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([NH:10][C:11]2[C:12]([OH:27])=[N:13][C:14]([C:17]3[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[O:19][N:18]=3)=[N:15][CH:16]=2)=[O:9])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178468674HCID 178468674, compound

Product 1

HCID 178524144HCID 178524144, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of compound 3-2 (60 mg, 0.135 mmol) in H2O (100 mL) was added KOH (75 mg, 1.35 mmol) and stirred at 50° C. for 30 min. The reaction mixture was extracted with EA (20 mL). The aqueous layer was adjusted to pH 3 by addition of HCl. The solids were filtered to afford compound 3-3 as a white solid (40 mg, 71%). 1H NMR (300 MHz, DMSO-d6) δ 13.61 (br s, 1H), 10.02 (s, 1H), 8.99 (s, 1H), 7.35-7.26 (m, 12H), 5.76 (s, 1H). LC-MS: (M+H)+ 417.

Workup

  1. extractionThe reaction mixture was extracted with EA (20 mL)
  2. additionThe aqueous layer was adjusted to pH 3 by addition of HCl
  3. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-339d05ae45884d87bb2906484d9313ef
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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