Hydrochloric Acid → 2-Amino-3-(4-methoxyphenyl)-2-methylpropanoic acid hydrochloride

HRID 78953Notes

Reaction equation

HRID 78953 reaction equation
[NH2:1][C:2]([CH3:19])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:3]([O:5]C(C)(C)C)=[O:4].C1(C)C=CC=CC=1.[ClH:27]>CC(O)C>[ClH:27].[NH2:1][C:2]([CH3:19])([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 67166510Tert-butyl 2-amino-3-(4-methoxyphenyl)-2-methylpropanoate

Product 1

HCID 671657322-Amino-3-(4-methoxyphenyl)-2-methylpropanoic acid hydrochlorideYield 67%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Intermediate tert-butyl 2-amino-3-(4-methoxyphenyl)-2-methylpropanoate (0.60 g, 2.26 mmol) was mixed with toluene (6 mL) and a 5-6 N HCl solution in IPA (2 mL). A clear yellow solution was heated to reflux and kept at that temperature for 7 h. The resulting slurry was cooled to ambient temperature and filtered. The solid was washed with toluene (3 mL) on a filter and air-dried to afford 2-amino-3-(4-methoxyphenyl)-2-methylpropanoic acid hydrochloride [0.37 g; 67%] as a white solid [HPLC 71.8% (AUC; tR=3.71]. 1H NMR (500 MHz, DMSO-d6): δ 13.96 (br. s, 1H, COOH), 8.44 (br. s, 3H, NH3), 7.16 (d, J=8.7 Hz, 2H, Ar), 6.90 (d, J=8.7 Hz, 2H, Ar), 3.74 (s, 3H, CH3), 3.08 (s, 2H, CH2), 1.48 (s, 3H, CH3). Optical rotation (α25D, DMSO, c=1.10)+7.27°.

Workup

  1. temperatureA clear yellow solution was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe solid was washed with toluene (3 mL) on
  5. filtrationa filter
  6. customair-dried

Sources & evidence

ORD record
ord-83119d52c8f24688b588647f2377ef86
Source dataset
uspto-grants-2014_09
Patent number
US08841486B2

Reaction notes

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