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

HRID 1901258Notes

Reaction equation

HRID 1901258 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=7 Hz, 3H), 3.02 (dd, J=10 Hz, J=15 Hz, 1H), 3.25 (dd, J=6 Hz, J=15 Hz, 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-55b0c36027cb46db90d9c46cd0789862
Source dataset
uspto-grants-1996_11
Patent number
US05576447

Reaction notes

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