Hydrochloric Acid → 239463-70-8

HRID 382474Notes

Reaction equation

HRID 382474 reaction equation
[C:1]([O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:23][C@H:24]([NH:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH2:37][CH3:38])[CH3:25])=[CH:17][C:18]=2[C:20](=[O:22])[NH2:21])[CH:13]=[CH:12]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[ClH:39]>C(O)C>[ClH:39].[C:1]([O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:23][C@H:24]([NH:26][CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH2:37][CH3:38])[CH3:25])=[CH:17][C:18]=2[C:20](=[O:22])[NH2:21])[CH:13]=[CH:12]1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9872508239463-68-4

Product 1

HCID 9872507239463-70-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-3-[7-carbamoyl-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-1H-indol-1-yl]propyl pivalate (6.07 g) in ethanol (58 ml) was added dropwise 1N hydrochloric acid (11.6 ml) under ice-cooling with stirring, and the mixture was stirred for 15 minutes under the same condition. The reaction mixture was concentrated in vacua, and to the residue was added ethanol. After azeotropic removal of water, the residue was dissolved in ethanol (6 ml) and ethyl acetate (60 ml) was added to the solution. After the mixture was allowed to stand for 16 hours at room temperature, the resulting colorless crude crystals (5.14 g) were obtained. After the crystals were combined with another crude crystals obtained similarly, recrystallization of the combined crystal (8.12 g) from ethanol/ethyl acetate (15/1) gave (R)-3-[7-carbamoyl-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-1H-indol-1-yl]propyl pivalate hydrochloride (7.46 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 minutes under the same condition
  3. concentrationThe reaction mixture was concentrated in vacua
  4. additionto the residue was added ethanol
  5. customAfter azeotropic removal of water
  6. dissolutionthe residue was dissolved in ethanol (6 ml)
  7. additionethyl acetate (60 ml) was added to the solution
  8. customthe resulting colorless crude crystals (5.14 g) were obtained
  9. customobtained similarly
  10. customrecrystallization of the combined crystal (8.12 g) from ethanol/ethyl acetate (15/1)

Sources & evidence

ORD record
ord-f1a697a8eb5f4c3f9fd73189fabc4496
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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