Hydrochloric Acid → tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

HRID 2184950Notes

Reaction equation

HRID 2184950 reaction equation
C(OC([NH:11][C@@H:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:23][CH:22]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1.Cl.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:11][C@@H:12]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:26]=1)[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11038228tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateYield 99.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

100 g (0.206 mol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-ethoxy-carbonylpropyloxy)phenyl)propionate (1.1) from Example 1 were dissolved in 1 liter of methanol, the solution was treated with methanolic hydrogen chloride solution and with 10 g of 20% palladium hydroxide/carbon and hydrogen was passed in for 6 hours. Then the catalyst was filtered off, the solution was evaporated and the residue was treated with tert-butylether. The precipitate formed was filtered off. 72 g (90%) of an amorphous powder were obtained.

Workup

  1. customwas passed in for 6 hours
  2. filtrationThen the catalyst was filtered off
  3. customthe solution was evaporated
  4. additionthe residue was treated with tert-butylether
  5. customThe precipitate formed
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-14a1ef49779c47edae65047b411f6ca6
Source dataset
uspto-grants-2002_06
Patent number
US06399620B1

Reaction notes

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