Acetone → HCID 66746925, compound

HRID 931409Notes

Reaction equation

HRID 931409 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:14])[C@H:7]([C:9]([CH2:12][OH:13])([CH3:11])[CH3:10])[OH:8].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:22][C:23]([CH3:25])=O>>[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C@H:7]1[C:9]([CH3:11])([CH3:10])[CH2:12][O:13][C:23]([CH3:25])([CH3:22])[O:8]1)=[O:14]

Participants

4

Reactant 3

HCID 180AcetoneHCID 24436Sodium SulfateHCID 5748487L-Panthenol

Product 1

HCID 66746925HCID 66746925, compoundYield 59%

Procedure

D-panthenol (10 mmol), anhydrous Na2SO4 (35.20 mmol) and PTSA monohydrate (0.99 mmol) was stirred in anhydrous acetone (40 mL) at room temperature during 4 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The crude was purified by chromatography on a silica gel column (eluent: CH2Cl2/CH3OH 0 to 10%) to give the expected compound as a white crystallized solid in 59% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 0.89 (s, 3H), 0.91 (s, 3H), 1.37 (s, 6H), 1.55 (quintuplet, J=6.52 Hz, 2H), 3.03-3.11 (m, 1H), 3.17-3.25 (m, 2H), 3.38-3.43 (m, 2H), 3.63 (d, J=11.48 Hz, 1H), 4.02 (s, 1H), 4.49 (t, J=5.18 Hz, 1H), 7.45-7.48 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe crude was purified by chromatography on a silica gel column (eluent: CH2Cl2/CH3OH 0 to 10%)

Sources & evidence

ORD record
ord-110984056ca84e4cb1cd78a778cf2d1b
Source dataset
uspto-grants-2016_03
Patent number
US09296778B2

Reaction notes

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