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

HRID 559456Notes

Reaction equation

HRID 559456 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 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. washwashed with ether
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-5a4e7247f13e4f39a8acd4a9b5539788
Source dataset
uspto-grants-2011_11
Patent number
US08063050B2

Reaction notes

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