L-Serine → 2-Methyl Oleoyl-L-Serine

HRID 218122

反応式

HRID 218122 の反応式
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH3:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:21](O)=[O:22]>O1CCCC1>[CH3:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:21]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])=[O:22]

参加物

6

反応物 4

HCID 5951L-SerineHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 99222352-Methyl oleic acid

生成物 1

HCID 469122122-Methyl Oleoyl-L-Serine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

A solution of L-serine (190 mg, 1.8 mmol) in 20 ml. of 0.1 N sodium carbonate and 0.1 N sodium bicarbonate was added to a solution of N-hydroxysuccinimide ester of 2-methyl oleic acid (204.5 mg, 0.5 mmole) in 20 ml tetrahydrofuran. The reaction mixture was stirred overnight at 35° C., evaporated down to 20 ml, and acidified to pH 1 with 1 N HCl. The product was extracted with methylene chloride (2×20 mL), dried (MgSO4), and the solvent evaporated under reduced pressure. The crude material was chromatographed on silica gel (eluting with chloroform:methanol) to give 86 mg (45%) as a yellowish oil 1H NMR (CDCl3) δ 0.912 (t, 3H), 1.129 (d, 3H), 1.288 (s, 20H), 1.611 (m, 2H), 2.018 (m, 4H), 2.323 (m. 1H), 3.787 (dd, 1H), 3.980 (dd, 1H), 4.503 (t, 1H), 5.353 (m, 2H).

後処理

  1. customevaporated down to 20 ml
  2. extractionThe product was extracted with methylene chloride (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude material was chromatographed on silica gel (eluting with chloroform:methanol)

出典と根拠

ORDレコード
ord-53031352c4a047ffac300995c5a3175e
出典データセット
uspto-grants-2012_06
特許番号
US08198327B2

関連ノート

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