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

HRID 375413Notes

Reaction equation

HRID 375413 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) δ1.03 (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-93b22013bb1e4c2296b046b817029cc4
Source dataset
uspto-grants-1996_01
Patent number
US05484946

Reaction notes

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