Palmitoyl chloride → (R)-3-(4-hydroxyphenyl)-2-palmitamidopropanoic acid

HRID 389049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389049
Cl.C[O:3][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].C(N(CC)CC)C.[C:23](Cl)(=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C(Cl)Cl>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C@@H:5]([NH:6][C:23](=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:4]([OH:3])=[O:15])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochloride

Produkt 1

HCID 6709897(R)-3-(4-hydroxyphenyl)-2-palmitamidopropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of L-Tyrosine methyl ester hydrochloride (1 g, 4.3 mmol) in CH2Cl2 was added triethylamine (1.49 mL, 8.6 mmol) at room temperature. Palmitoyl chloride (1.53 g, 5.6 mmol) was then added to the reaction mixture at 0° C. After the reaction was completed, as judged by TLC, the reaction mixture was quenched and extracted with 1 N HCl (3×5 mL) then saturated sodium bicarbonate (1×5 mL). The combined organic layers were dried with Na2SO4 and evaporated under vacuum to a white solid (1.86 g, 4.3 mmol). The product was carried on without further purification. 1H NMR (300 MHz, CDCl3, 23° C., 6): 6.94 (d, 1H, J=8.5), 6.73 (d, 1H, J=8.5), 5.92 (d, 1, H, J=8.0), 4.90 (d, 1H, J=5.8), 4.85 (d, 1H, J=5.8), 3.73 (s, 3H), 3.04 (ddd, 1H, J=5.8, 14.0, 27.7), 2.26-2.12 (m, 1H), 1.58 (m, 2H), 1.25 (m, 24H), 0.90 (t, 3H, J=6.67).

Aufarbeitung

  1. customthe reaction mixture was quenched
  2. extractionextracted with 1 N HCl (3×5 mL)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. customThe product was carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-7d5a039bd1c94e73997884ddbc24a476
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378100B2

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