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

HRID 1725273Notes

Reaction equation

HRID 1725273 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

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)−.

Workup

  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)

Sources & evidence

ORD record
ord-e3041fe5b4fe402db2edf730f4ea2d1c
Source dataset
uspto-grants-2009_02
Patent number
US07488829B2

Reaction notes

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