2-Dimethylaminopyridine → Hexadecanoic acid (2-oxo-4-pentadec-1-enyl-[1,3]dioxan-5-yl)-amide

HRID 45978Notes

Reaction equation

HRID 45978 reaction equation
[C:1]([NH:18][C@H:19]([C@@H:22](/[CH:24]=[CH:25]/[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[OH:23])[CH2:20][OH:21])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:41](=[O:42])C1.CN(C1C=CC=CN=1)C>C1COCC1>[O:42]=[C:41]1[O:23][CH:22]([CH:24]=[CH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:19]([NH:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:20][O:21]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 676246Di(succinimido) carbonateHCID 5283564C16-Ceramide

Product 1

HCID 66790703Hexadecanoic acid (2-oxo-4-pentadec-1-enyl-[1,3]dioxan-5-yl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-palmitoylsphingosine (C16-ceramide, 1.61 g, 3 mmol) was dissolved in dry THF (100 ml) with heating. The clear solution was brought to room temperature and N,N′-disuccinimidyl carbonate (1.92 g, 7.5 mmol) was added. Dimethylaminopyridine (DMAP 0.81 g, 7.5 mmol) was added with stirring and the reaction further stirred for 16 hours. The solvent was removed under reduced pressure and the residue was re-crystallized from n-heptane yielding 1.3 g (68%) of disuccinimidylceramidyl carbonate as white powder m.p. 73-76° C.

Workup

  1. temperaturewith heating
  2. customwas brought to room temperature
  3. customthe reaction
  4. stirringfurther stirred for 16 hours
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was re-crystallized from n-heptane yielding 1.3 g (68%) of disuccinimidylceramidyl carbonate as white powder m.p. 73-76° C.

Sources & evidence

ORD record
ord-abf6e0ea3c46465c801339b128107511
Source dataset
uspto-grants-2013_09
Patent number
US08541605B2

Reaction notes

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