delta-Gluconolactone → dodecyl L-alaninate

HRID 441113

反応式

HRID 441113 の反応式
C1(=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.[CH2:13]([O:25][C:26](=[O:30])[CH:27]([CH3:29])[NH2:28])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>C(O)(C)C>[NH2:28][C@H:27]([C:26]([O:25][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:30])[CH3:29]

参加物

5

反応物 3

HCID 7027delta-GluconolactoneHCID 8471TriethylamineHCID 6453806Dodecyl 2-aminopropanoate

生成物 1

HCID 181533dodecyl L-alaninate収率 73%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

反応条件

温度
60 °C

実験手順

A 100 ml round bottom flask equipped with a condenser, addition funnel, thermometer and mechanical stirrer was charged with D-glucono-1,5-lactone (7.0 g, 0.04 mole) and isopropanol (30 g). The suspension was heated to 60° C. over 15 minutes. A mixture of DL-alanine dodecyl ester ptoluenesulfonate salt (16.9 g, 0.04 mole), triethylamine (4.0 g 0.04 mole) and isopropanol (20 g) were added dropwise over 15 minutes from an addition funnel. The reaction mixture was stirred rapidly for about 6 hrs and then cooled to room temperature. The white product was filtered, washed with chloroform (3×150 ml) and dried under high vacuum at 35° C. giving 12.5 g (73% yield) of N-D-gluconyl dodecyl alaninate with a melting point of 97°-98° C. and 98.8% purity.

後処理

  1. customA 100 ml round bottom flask equipped with a condenser, addition funnel
  2. additionwere added dropwise over 15 minutes from an addition funnel
  3. temperaturecooled to room temperature
  4. filtrationThe white product was filtered
  5. washwashed with chloroform (3×150 ml)
  6. customdried under high vacuum at 35° C.

出典と根拠

ORDレコード
ord-39ad4ba91e1d458da23483f42f65a133
出典データセット
uspto-grants-1996_05
特許番号
US05521293

関連ノート

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