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

HRID 2258155Notes

Reaction equation

HRID 2258155 reaction equation
[ClH:1].CC(C)(OC([NH:8][C@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)C>CCOC(C)=O>[ClH:1].[NH2:8][C@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15471178Ethyl (3R)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate

Product 1

HCID 22831526(S)-Ethyl 3-amino-3-phenylpropanoate hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dry HCl gas was bubbled through a solution of the product of example 12 (3.0 g, 10.2 mmol) in EtOAc (50 mL) at ambient temperature for 15 minutes. After stirring for an additional 30 minutes, the solvent was removed under reduced pressure affording 2.30 g (98%) of product as a yellow oil. 1H-NMR (300 MHz, d6 -DMSO) δ 1.03 (t, J=7Hz, 3H), 3.02 (dd, J=10Hz, J=15Hz, 1H), 3.25 (dd, J=6Hz, J=15Hz, 1H), 3.96 (m, 2H), 4.55 (m, 1H), 7.3-7.6 (m, 5H), 8.93 (s, 3H).

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-26f48a342fae4d0295008eb0984c125a
Source dataset
uspto-grants-1997_08
Patent number
US05659063

Reaction notes

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