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

HRID 1612518노트

반응식

HRID 1612518 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 10340Sodium Carbonate용매

실험 절차

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)−.

후처리

  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)

출처 및 근거

ORD 기록
ord-f8eca69436454cfdba0fa00bbe84e2b9
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992067B2

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