Aldono-1,5-lactone → 12-(2,3,4,5,6-Pentahydroxyhexanoylamino)dodecanoic acid

HRID 1612518ノート

反応式

HRID 1612518 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[OH:16][CH:17]1[CH:22]([OH:23])[CH:21]([OH:24])[CH:20]([CH2:25][OH:26])[O:19][C:18]1=[O:27]>CO.C(=O)([O-])[O-].[Na+].[Na+]>[OH:19][CH:20]([CH:21]([OH:24])[CH:22]([OH:23])[CH:17]([OH:16])[CH2:18][OH:27])[C:25]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:26]

参加物

5

反応物 2

HCID 736Aldono-1,5-lactoneHCID 6966112-Aminododecanoic Acid

生成物 1

HCID 2225203412-(2,3,4,5,6-Pentahydroxyhexanoylamino)dodecanoic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 10340Sodium Carbonate溶媒

実験手順

3.5 g of 12-aminododecanoic acid are dissolved in 500 ml of methanol and, with 2.7 g of finely powdered sodium carbonate and 4.8 g of 3,4,5-trihydroxy-6-hydroxymethyltetrahydropyran-2-one, stirred at room temperature for 30 hours. The mixture is filtered off, the filtrate is concentrated and the residue is dissolved in 70 ml of water. With ice-cooling, 1N hydrochloric acid is added gradually until the pH is 1–2 (about 50–55 ml). The free acid precipitates out and is filtered off with suction, washed with a little cold water, and dried under high vacuum at 35° C. This gives 9 of molecular weight 393.48 (C18H35NO8); MS (ESI+): 394 (M+H+); (ESI−):392 (M−H)−.

後処理

  1. filtrationThe mixture is filtered off
  2. concentrationthe filtrate is concentrated
  3. dissolutionthe residue is dissolved in 70 ml of water
  4. temperatureWith ice-cooling
  5. addition1N hydrochloric acid is added gradually until the pH is 1–2 (about 50–55 ml)
  6. customThe free acid precipitates out
  7. filtrationis filtered off with suction
  8. washwashed with a little cold water
  9. customdried under high vacuum at 35° C
  10. customThis gives 9 of molecular weight 393.48 (C18H35NO8)

出典と根拠

ORDレコード
ord-f8eca69436454cfdba0fa00bbe84e2b9
出典データセット
uspto-grants-2006_01
特許番号
US06992067B2

反応ノート

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