Hydrochloric Acid → (S)-Ethyl 3-amino-3-phenylpropanoate hydrochloride

HRID 636252Notes

Reaction equation

HRID 636252 reaction equation
C(OC([NH:11][C@H:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)C1C=CC=CC=1.[ClH:25]>C(O)C.[Pd]>[ClH:25].[NH2:11][C@H:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10853646Ethyl (S)-3-benzyloxycarbonylamino-3-phenylpropionate

Product 1

HCID 22831526(S)-Ethyl 3-amino-3-phenylpropanoate hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

10.29 g of ethyl (S)-3-benzyloxycarbonylamino-3-phenylpropionate (31.44 mmol) are dissolved in 125 ml of ethanol and hydrogenated catalytically over Pd/active charcoal at a Ph of 4 using an automated burette and while adding 2N ethanolic HCl. The catalyst is filtered off with suction through kieselguhr and the filtrate is concentrated. The residue is triturated with diethyl ether, filtered off with suction, washed with diethyl ether and dried over phosphorus pentoxide.

Workup

  1. filtrationThe catalyst is filtered off with suction through kieselguhr
  2. concentrationthe filtrate is concentrated
  3. customThe residue is triturated with diethyl ether
  4. filtrationfiltered off with suction
  5. washwashed with diethyl ether
  6. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-766cc0a2a5d545279583cb5aa9d23d48
Source dataset
uspto-grants-2001_02
Patent number
US06191282B1

Reaction notes

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