Triethylamine → (R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide

HRID 74116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74116
[NH2:1][C@H:2]([CH2:13][OH:14])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25]>O1CCCC1>[CH2:6]([NH:5][C:3](=[O:4])[C@H:2]([NH:1][C:22]([O:23][CH2:24][CH3:25])=[O:26])[CH2:13][OH:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10655432(2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

Produkt 1

HCID 53344986(R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamideAusbeute 73,04 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 250 mL three-neck round bottom flask, 9.65 g (0.0497 mol) (R)-2-amino-N-benzyl-3-hydroxypropionamide, 120 mL tetrahydrofuran, and 7.58 g (0.0749 mol) triethylamine were added in sequence, the mixture was stirred to obtain a solution. At a normal temperature, 6.01 g (0.0554 mol) ethyl chlorocarbonate was added. After the reaction was completed, the solvent was evaporated, and the residue was added with 100 mL water, and stirred uniformly. The solution was extracted with 50 mL×3 ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was evaporated, to obtain a white solid of 9.67 g (0.0363 mol). The molar yield was 73.04%.

Aufarbeitung

  1. customto obtain a solution
  2. customthe solvent was evaporated
  3. additionthe residue was added with 100 mL water
  4. stirringstirred uniformly
  5. extractionThe solution was extracted with 50 mL×3 ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customto obtain a white solid of 9.67 g (0.0363 mol)

Quellen und Nachweise

ORD-Eintrag
ord-8967ae5b38804f6ca2b764f681026423
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829226B2

Notizen zur Reaktion

Wird geladen…