Hydrochloric Acid → HCID 67289220, compound

HRID 511855Notes

Reaction equation

HRID 511855 reaction equation
C[O:2][C:3]([C:5]1[N:6](C(OC(C)(C)C)=O)[C:7]2[C:12]([CH:13]=1)=[C:11]([CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[CH:10]=[CH:9][CH:8]=2)=[O:4].[OH-].[Na+].Cl>C1COCC1>[N:15]1([CH2:14][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:12]=2[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[NH:6]3)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131733272HCID 131733272, compound

Product 1

HCID 67289220HCID 67289220, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 4-Imidazol-1-ylmethyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methy ester (350 mg, 0.99 mmol) and 2N aqueous sodium hydroxide solution (1 mL. 2 mmol) in THF (5 mL) was refluxed at 80° C. with stirring for 2 days. 2N hydrochloric acid was added until pH was 7.0. The mixture was concentrated in vacuo. The resulting percipitate was collected by filtration and washed with dichloromethane, methanol, H2O and ethyl acetate to give 63 mg (27% yield) of the title compound as a white solid:

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe resulting percipitate was collected by filtration
  3. washwashed with dichloromethane, methanol, H2O and ethyl acetate

Sources & evidence

ORD record
ord-614f428daa2140ddb37ae5d4a25f54fb
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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