Potassium Hydroxide → HCID 66841531, compound

HRID 1929098Notes

Reaction equation

HRID 1929098 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-e4be19c0914a4fe298b14ec3f6a53c63
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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