Methanol → Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

HRID 1940084Notes

Reaction equation

HRID 1940084 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9].[CH3:21]O>>[ClH:3].[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH2:7][C:8]([O:10][CH3:21])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 5971823-Amino-3-(3,4-dimethoxyphenyl)propanoic acid

Product 1

HCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochlorideYield 66%

Conditions

Temperature
0 °C

Procedure

To 150 mL of stirred methanol at 0° C. under nitrogen was slowly added thionyl chloride (14.2 mL, 194.4 mmol). To the reaction mixture was then added 3-amino-3-(3,4-dimethoxyphenyl)propionic acid (15.5 g, 64.8 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature, and stirred overnight. The reaction solution was concentrated to an oil and then diluted with 200 mL of CH3OH/Et2O (1/3) and stirred. The resulting slurry was filtered and the solid was washed with a copious amount of ether. The solid was dried in vacuo (60° C., <1 mm) to afford 1.83 g (66%) of methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride as a white powder: 1H NMR (DMSO-6, 250 MHz) δ8.59 (br s, 3H, NH3), 6.9-7.3 (m, 3H, Ar), 4.52 (overlapping dd, 1H), 3.77 (s, 3H, OCH3), 3.75 (s, 3H, OCH3), 3.67 (s, 3H, OCH3), 3.16 (dd, 1H, J1 =6 Hz, J2 =16 Hz), 2.98 (dd, 1H, J1 =8 Hz. J2 =16 Hz); 13C NMR (DMSO-d6) δ169.6, 149.0, 129.0, 120.0, 111.5, 111.4, 55.7, 55.5, 51.7, 50.8, 38.5. Anal. Calcd for C12 H18NO4Cl. Theoretical C, 52.27; H, 6.58; N, 5.08. Found C, 52.44; H, 6.53; N, 5.01.

Workup

  1. customat 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. concentrationThe reaction solution was concentrated to an oil
  5. additiondiluted with 200 mL of CH3OH/Et2O (1/3)
  6. stirringstirred
  7. filtrationThe resulting slurry was filtered
  8. washthe solid was washed with a copious amount of ether
  9. customThe solid was dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-0ce37a2fd22840e98e3a32ca598f6d68
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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