HCID 11348669, compound → HCID 15434243, compound

HRID 611615Notes

Reaction equation

HRID 611615 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C@@H:11]([OH:24])[CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[O:24]1[CH2:12][C@H:11]1[C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 11348669HCID 11348669, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15434243HCID 15434243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-toluene-4-sulfonic acid 2-(6-acetylamino-pyridin-3-yl)-2-hydroxy-ethyl ester (200 g, 0.57 mol) in THF (2.4 L) was cooled to -15° C. and potassium t-butoxide (542 ml, 0.542 mol, 1M in THF) was added slowly at -15° C. to -10° C. over a two hour period. Stirring was continued at -15° C. for an additional 40 minutes. The reaction mixture was filtered with the aid of Celite®. The filtration was done through cloth precoated with Celite®. The filter cake was washed with tetrahydrofuran. The filtrate was concentrated under vacuum to afford 300 ml of an oil. The oil was diluted with 1.2 liters of hexanes which resulted in the formation of a solid. The suspension was stirred at room temperature for one hour to granulate the solid. The suspension was filtered and the filtrate was washed with hexanes to afford 80.0 g (78.8%) of the title product as a solid. mp 96-98° C. 1H NMR (CDCl3): δ=8.70 (br, 1 H); 8.21 (m, 2 H); 7.57 (d of d, 1 H); 3.86 (m, 1 H); 3.17 (m, 1 H); 2.83 (m, 1 H); 2.19 (s, 3 H). MS (Cl): m/z=179 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered with the aid of Celite®
  2. filtrationThe filtration
  3. washThe filter cake was washed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-60b1eaf77f9d4945b41e5e8dc293ba0e
Source dataset
uspto-grants-1999_12
Patent number
US06001856

Reaction notes

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