Potassium Carbonate → HCID 22905639, compound

HRID 1488469Notes

Reaction equation

HRID 1488469 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:19])[C:9]([O:15]C(=O)C)=[C:10]([CH3:14])[C:11]=2[CH3:13])[CH:6]([CH3:20])[CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:19])[C:9]([OH:15])=[C:10]([CH3:14])[C:11]=2[CH3:13])[CH:6]([CH3:20])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22905647HCID 22905647, compound

Product 1

HCID 22905639HCID 22905639, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Deacetylation of 29a was achieved by reaction with potassium carbonate in methanol according to the procedure of Burkalova, et al., Biofizika 1980, 24, 989. Purification of crude material by flash column chromatography on silica gel using a solvent system of ethyl acetate/Skellysolve B (6:4, Rf =0.18) afforded 29b as a white solid, nap 171°-173° C. Spectral data: IR (Nujol) 3500, 1635, 1400, 1210 cm-1 ; 1H NMR (CD3SOCD3): δ 1.05 (d, 3H), 1.90 (br s, 3H), 2.10 (2 partially resolved s, 3H each), 2.15 (br s, 3H), 3.10 (br m, 1H), 3.75 (br m, 1H), 3.85 (br m, 1H), 7.85 (br s, 1H); 13C NMR (CD3 SOCD3): δ 12.34, 12.64, 17.42, 18.10, 23.50, 35.44, 58.25, 117.49, 121.94, 124.93, 133.47, 135.81, 150.41, 168.58; CI-MS: m/z 234 (MH+, base), 172, 154, 136; CI-HRMS: Calcd. for C14H20 NO2 (M+H+) 234.1494, fnd. 234.1494. Anal: calcd. for C14 H19NO2C, 72.07, H, 8.21, N, 6.00, fnd. C, 71.85, H, 8.24, N, 5.92.

Workup

  1. customPurification of crude material by flash column chromatography on silica gel using a solvent system of ethyl acetate/Skellysolve B (6:4, Rf =0.18)

Sources & evidence

ORD record
ord-53e78230158b4cc8ba1398b65d3e3111
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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