Acetone → HCID 59883971, compound

HRID 1427747Notes

Reaction equation

HRID 1427747 reaction equation
Cl.CO[C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6].[CH3:16][NH2:17].CO.[CH3:20][C:21]([CH3:23])=O>>[OH:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@@H:5]2[NH:6][C:21]([CH3:23])([CH3:20])[N:17]([CH3:16])[C:4]2=[O:15])=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 6329MethylamineHCID 76956Methyl tyrosinate hydrochloride

Product 1

HCID 59883971HCID 59883971, compound

Procedure

(S)-tyrosine methyl ester hydrochloride (23 g, 100 mmol) was added to an ethanolic solution of MeNH2 (60 mL, 8 M), and the resulting mixture was stirred at room temperature for 24 h. The excess MeNH2 was removed by distillation or by washing with THF several times until the N-methyl amide product was obtained as a white solid. Dry MeOH (200 mL) and dry acetone (40 mL) were added to this residue. The resulting solution was stirred at 60° C. for 24 h, cooled to room temperature, and then concentrated in vacuo. Compound 2 was obtained as a white solid in 82% overall yield (19.2 g, 82 mmol) after silica gel chromatography (1:1 of EtOAc:Hex). 1H NMR (CDCl3): δ 7.09 (d, 2H), 6.74 (d, 2H), 3.82 (t, 1H), 3.06 (m, 2H), 2.78 (s, 3H), 1.32 (s, 3H), 1.22 (s, 3H). Elemental analysis for C13H18N2O2 (2)—calculated: C 66.64, H 7.74, N 11.96%; observed: C 66.24, H 7.70, N 12.10%.

Workup

  1. customThe excess MeNH2 was removed by distillation
  2. washby washing with THF several times until the N-methyl amide product
  3. customwas obtained as a white solid
  4. stirringThe resulting solution was stirred at 60° C. for 24 h
  5. temperaturecooled to room temperature
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7481ab2ef9914c359237dcba11562a82
Source dataset
uspto-grants-2015_01
Patent number
US08933276B2

Reaction notes

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