Hydrochloric Acid → (s)-Ethyl 3-amino-3-(3-nitrophenyl)propanoate hydrochloride salt

HRID 735592Notes

Reaction equation

[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)([Cl:18])=O.[CH2:20](O)[CH3:21].Cl>O1CCOCC1>[ClH:18].[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:3][C:4]([O:6][CH2:20][CH3:21])=[O:5]

Participants

Conditions

Temperature: -10 °C

Procedure

(S)-3-Amino-3-(3-nitrophenyl)propanoic acid (500 mg, 2.4 mmol) was dissolved in 2.0HCl in dioxane (2 mL) and concentrated in vacuo. In a separate flask thionyl chloride (0.21 mL, 2.8 mmol) was added to ethanol at −10° C. The ethanolic solution was stirred for 20 min at −10° C. then added to the HCl salt of (S)-3-amino-3-(3-nitrophenyl)propanoic acid. The resulting solution was stirred at ambient temperature for 1 h and at 40° C. for 3 h. The reaction mixture was concentrated in vacuo to yield 34A (600 mg, 92%) as a white solid. MS (ESI) m/z 239.09 (M+H)+.

Workup

concentrationconcentrated in vacuo
stirringThe resulting solution was stirred at ambient temperature for 1 h and at 40° C. for 3 h
concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-fabc1dade65d4918b32873729320a8e8
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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