Hydrochloric Acid → (3s)-3-(2-(r,s)-Hydroxydodecylamino)-3-phenylpropionic acid

HRID 2386112Notes

Reaction equation

HRID 2386112 reaction equation
C[O-].[Na+].[NH2:4][C@H:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8].[O:16]1[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17]1.Cl>CO>[OH:16][CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17][NH:4][C@H:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 178581,2-EpoxydodecaneHCID 686704(3S)-3-amino-3-phenylpropanoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 66661964(3s)-3-(2-(r,s)-Hydroxydodecylamino)-3-phenylpropionic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

27.01 g of sodium methoxide and 82.6 g of (S)-3-amino-3-phenylpropionic acid were dissolved in 800 ml of methanol. After adding 92 g of 1,2-epoxydodecane, the solution was stirred at room temperature for 20 h. Subsequently, the pH of the solution was adjusted to pH 6 with methanolic hydrochloric acid and the sodium chloride which crystallized out filtered off. After the methanol was distilled off, an oily residue remained, which crystallized in the course of stirring with 700 ml of acetone. This resulted in 153.4 g of colorless crystals. 1H NMR (DMSO) δ (ppm): 0.85 (t, 3H), 1.13-1.31 (m, 18H), 2.28/2.60/2.70/2.86 (m, 2H), 3.02 (m, 1H), 3.34 (m, 1H), 3.66-3.78 (m, 1H), 4.57 (m, 1H), 5.20/5.29 (s, br., 1H, OH), 7.42 (m, 3H), 7.60 (m, 2H), 9.40 (s, br., 2H, NH2+), 12.56 (s, 1H, CO2H)

Workup

  1. customthe sodium chloride which crystallized out
  2. filtrationfiltered off
  3. distillationAfter the methanol was distilled off
  4. customwhich crystallized in the course
  5. stirringof stirring with 700 ml of acetone

Sources & evidence

ORD record
ord-a0a20dcfa7b84e8a9b82e6df4f4d57a1
Source dataset
uspto-grants-2012_09
Patent number
US08268631B2

Reaction notes

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