Acetone → HCID 53483228, compound

HRID 1427748Notes

Reaction equation

HRID 1427748 reaction equation
Cl.CO[C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[CH2:15]([CH2:17][NH2:18])[OH:16].CO.[CH3:21][C:22]([CH3:24])=O>>[CH2:7]([C@@H:5]1[NH:6][C:22]([CH3:24])([CH3:21])[N:18]([CH2:17][CH2:15][OH:16])[C:4]1=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 700EthanolamineHCID 887MethanolHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 53483228HCID 53483228, compound

Procedure

(S)-phenylalanine methyl ester hydrochloride (21.5 g, 100 mmol) was added to ethanolamine (48 mL, 800 mmol), and the resulting mixture was stirred at room temperature for 24 h. The excess ethanolamine was removed by distillation until the N-(2-hydroxylethyl) 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 6 was obtained as a white solid in 55% overall yield (13.6 g, 55 mmol) after silica gel chromatography (2:1 of EtOAc:Hex). 1H NMR (CDCl3): δ 7.2-7.34 (m, 5H), 3.85 (t, 1H), 3.60-3.70 (m, 2H), 3.42 (m, 1H), 3.14 (m, 2H), 3.09 (d, 2H), 1.28 (s, 3H), 1.13 (s, 3H). Elemental analysis for C14H20N2O2 (6)—calculated: C 67.71, H 8.12, N 11.28%; observed: C 67.12, H 7.99, N 11.52%.

Workup

  1. customThe excess ethanolamine was removed by distillation until the N-(2-hydroxylethyl) amide product
  2. customwas obtained as a white solid
  3. stirringThe resulting solution was stirred at 60° C. for 24 h
  4. temperaturecooled to room temperature
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3dd63459a6b4c9f8674b274bb4e2731
Source dataset
uspto-grants-2015_01
Patent number
US08933276B2

Reaction notes

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