Fluoroacetic acid → N-Fluoroacetyl sphingosine

HRID 482128Notes

Reaction equation

HRID 482128 reaction equation
[OH:1][CH2:2][C@@H:3]([C@@H:5](/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[OH:6])[NH2:4].[Na].[F:23][CH2:24][C:25](O)=[O:26].[I-].ClC1C=CC=CN1C>CN(C)C=O.C(N(CC)CC)C>[F:23][CH2:24][C:25]([NH:4][C@H:3]([C@@H:5](/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[OH:6])[CH2:2][OH:1])=[O:26]

Participants

7

Reactant 4

HCID 5237Fluoroacetic acidHCID 5280335SphingosineHCID 5360545SodiumHCID 224484232-Chloro-1-methylpyridine iodide

Product 1

HCID 131719401N-Fluoroacetyl sphingosine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

5.0 gr of sphingosine (16.70) mM), prepared according to Example 4, are reacted with 2.1 gr of the sodium salt of fluoroacetic acid (20.88 mM), in the presence of 5.3 gr of 2-chloro-1-methylpyridine iodide (20.88 mM) and 5.8 cc of triethylamine (42.00 mM) in 80 cc of dimethylformamide, at room temperature overnight. The solvent is evaporated, and the residue is gathered in CH2Cl2 and washed with H2O. It is anhydrified and purified by chromatography, eluting with a mixture of CH2 Cl2 /ethyl acetate/CH3CH 70:30:1 v/v/v.

Workup

  1. customThe solvent is evaporated
  2. washwashed with H2O
  3. custompurified by chromatography
  4. washeluting with a mixture of CH2 Cl2 /ethyl acetate/CH3CH 70:30:1 v/v/v

Sources & evidence

ORD record
ord-20ec3f5d50784080845d146b4879883b
Source dataset
uspto-grants-1998_08
Patent number
US05792858

Reaction notes

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