Potassium Hydroxide → HCID 66841531, compound

HRID 2267807Notes

Reaction equation

HRID 2267807 reaction equation
CC[O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[C:21]3[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=3[O:19][CH:18]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5].[OH-].[K+]>C1COCC1.C(O)C.O>[F:26][C:24]1[CH:23]=[CH:22][C:21]2[C:17]([CH2:16][O:15][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:13]=3[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]4)=[CH:18][O:19][C:20]=2[CH:25]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 668416574-(6-Fluoro-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 66841531HCID 66841531, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

112 (1.2 g, 2.6 mmol) is dissolved in 30 ml of a 1:1:1 mixture of THF, ethanol and water. And after addition of KOH pellets (742 mg, 13.2 mmol) the mixture is stirred for 2 h (TLC control) at 85° C. Then the organic solvent are removed under reduced pressure. The residue is cooled to 0° C. and treated with 2M HCl. The crude product is filtered off and dried under high vacuum. The crude product (800 mg) is recrystallized from ethyl acetate.

Workup

  1. customThen the organic solvent are removed under reduced pressure
  2. temperatureThe residue is cooled to 0° C.
  3. additiontreated with 2M HCl
  4. filtrationThe crude product is filtered off
  5. customdried under high vacuum
  6. customThe crude product (800 mg) is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6b1d2c07aee34e4aa854db43a5c3e6ba
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

Loading…