Hydrochloric Acid → 239463-68-4

HRID 382473Notes

Reaction equation

HRID 382473 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]([N:26](C(OC(C)(C)C)=O)[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].Cl.C(=O)(O)[O-].[Na+]>C(O)(C)C.O>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12074059HCID 12074059, compound

Product 1

HCID 9872508239463-68-4Yield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

(R)-3-[5-[2-[N-(tert-Butoxycarbonyl)-N-[2-(2-ethoxy-phenoxy)ethyl]amino]propyl]-7-carbamoyl-1H-indol-1-yl]propyl pivalate (7.81 g) was dissolved in isopropanol (78 ml), and concentrated hydrochloric acid (39 ml) was added dropwise over a period of 10 minutes to the solution under ice-cooling with stirring. After the mixture was stirred for 4 hours at room temperature, the reaction mixture was adjusted to pH 8 by adding sodium bicarbonate powder under ice-cooling with stirring. The mixture was diluted with water (200 ml) and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution, water and brine subsequently, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate) and recrystallized from diethyl ether/hexane(2/1) to give (R)-3-[7-carbamoyl-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-1H-indol-1-yl]propyl pivalate (5.21 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringAfter the mixture was stirred for 4 hours at room temperature
  3. temperaturecooling
  4. stirringwith stirring
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with a saturated aqueous sodium bicarbonate solution, water and brine subsequently
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate)
  10. customrecrystallized from diethyl ether/hexane(2/1)

Sources & evidence

ORD record
ord-b357eabfc2be4876ae7cfde6c8a25edc
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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