Hydrochloric Acid → Methyl 3-amino-2-(4-chlorophenyl)propanoate hydrochloride

HRID 82409Notes

Reaction equation

HRID 82409 reaction equation
C(OC([NH:8][CH2:9][CH:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12])=O)(C)(C)C.Cl>O1CCOCC1.CCOCC>[ClH:21].[NH2:8][CH2:9][CH:10]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66617917Methyl 3-(Boc-amino)-2-(4-chlorophenyl)propanoate

Product 1

HCID 66617900Methyl 3-amino-2-(4-chlorophenyl)propanoate hydrochlorideYield 178.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of methyl 3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoate (4 mg, 1.44 mmol) in dioxane (6.0 mL) was treated with 4M HCl in dioxane (about 6.0 mL, 23.0 mmol) at room temperature. The mixture was stirred for 18 hours to completion, after which the reaction mixture was diluted with ether to afford a precipitate. The slurry was filtered under nitrogen to afford a white solid, which was washed with ether. The solid was dried under vacuum to afford the methyl 3-amino-2-(4-chlorophenyl)propanoate hydrochloride as a white solid (321 mg, 89%). LCMS (APCI+) m/z 214.0 [M+H]+.

Workup

  1. customto afford a precipitate
  2. filtrationThe slurry was filtered under nitrogen
  3. customto afford a white solid, which
  4. washwas washed with ether
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-b87c12c2a25949d4a7e27e1e34daf3b9
Source dataset
uspto-grants-2014_09
Patent number
US08846681B2

Reaction notes

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