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

HRID 389049ノート

反応式

HRID 389049 の反応式
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

参加物

5

反応物 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7d5a039bd1c94e73997884ddbc24a476
出典データセット
uspto-grants-2013_02
特許番号
US08378100B2

反応ノート

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