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

HRID 389049노트

반응식

HRID 389049 반응식
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

참가 물질

5

반응물 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7d5a039bd1c94e73997884ddbc24a476
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378100B2

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