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

HRID 240232
Notes
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Reaction equation

HRID 240232 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent

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-301adbb9d4b9442e98ab170d47998e12
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08647882B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes