Potassium Hydroxide → HCID 59152664, compound

HRID 1804792Notes

Reaction equation

HRID 1804792 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]([O:26][CH2:27][CH3:28])=[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>[CH2:27]([O: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)[CH3:28]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 673604314-(6-Ethoxy-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 59152664HCID 59152664, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

4-(6-Ethoxy-benzofuran-3-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (29a) (7.5 g, 15.6 mmol) is dissolved in 150 ml of a 1:1:1 mixture of THF, ethanol and water. And after addition of KOH pellets (4.4 g, 78.2 mmol) the mixture is stirred for 2 h (TLC control) at 85° C. Then the organic solvent is 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 is recrystallized from ethyl acetate.

Workup

  1. customThen the organic solvent is 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 is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-63b8d52de34f413786b7200f714685e3
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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