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

HRID 532792Notes

Reaction equation

HRID 532792 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 (451 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-c75e72f70dab4b7e8cf0f264d981f235
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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