Acetic Anhydride → 3-acetyl-3-[(E,15R,16S)-16-amino-15,17-dihydroxyheptadec-13-enyl]pentane-2,4-dione

HRID 2215286Notes

Reaction equation

HRID 2215286 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C@@H:16]([OH:21])[C@@H:17]([NH2:20])[CH2:18][OH:19].C(O[C:26](=[O:28])[CH3:27])(=O)C>N1C=CC=CC=1>[C:18]([C:1]([C:26](=[O:28])[CH3:27])([C:16](=[O:21])[CH3:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C@@H:16]([OH:21])[C@@H:17]([NH2:20])[CH2:18][OH:19])(=[O:19])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5280335Sphingosine

Product 1

HCID 1296328723-acetyl-3-[(E,15R,16S)-16-amino-15,17-dihydroxyheptadec-13-enyl]pentane-2,4-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a procedure similar to Grode and Cardellina D-erythro-sphingosine (4, 2 mg, 6.7 μmol, Sigma) in acetic anhydride (1 ml) and pyridine (2 ml) was stirred at 25° C. for 4.5 h, at which time no starting material could be observed by TLC. The solvent was removed by a stream of nitrogen to give 133: white solid; silica TLC Rf 0.86 (3:12:2:2 CHCl3/1-BuOH/AcOH/H2O, phosphomolybdic acid), 0.65 (9:1 CHCl3/MeOH, phosphomolybdic acid); FABMS m/z 580, 426, 366, 306, 264; CIMS m/z 468, 454, 426, 424, 394, 366, 364, 306, 264, 144, 85, 84, 83, 61.

Workup

  1. customThe solvent was removed by a stream of nitrogen

Sources & evidence

ORD record
ord-77588d48a2ff4bc28da3f9a265f460c8
Source dataset
uspto-grants-2006_09
Patent number
US07109244B2

Reaction notes

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