(R)-camphorsulfonic acid → HCID 86668042, compound

HRID 538332Notes

Reaction equation

HRID 538332 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([Br:16])[CH:11]=1)([CH2:8][OH:9])[CH2:6][OH:7])[CH3:2].[C@@:18]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:24]1)C[C:19]2=O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Br:16])[CH:11]=2)[CH2:8][O:9][C:18]([CH3:24])([CH3:19])[O:7][CH2:6]1)=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 131278(R)-camphorsulfonic acidHCID 866680414-Pyridineacetic acid, 2-bromo-α,α-bis(hydroxymethyl)-, ethyl ester

Product 1

HCID 86668042HCID 86668042, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-bromo-pyridin-4-yl)-3-hydroxy-2-hydroxymethyl-propionic acid ethyl ester (30.0 g, 98.6 mmol) 2,2-dimethoxy propane (51.11 g, [60.5 ml], 493.1 mmol) and (1R)-(−)-10-camphor sulphonic acid (5.72 g, 24.65 mmol) in DMF (100 ml) was heated at 80° C. for 10 h. Reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and worked up by washing with water, brine, followed by drying over anhy. Na2SO4. Organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography using 10% ethyl acetate in Hexane to obtain title compound as a yellow solid. Yield=18.15 g (53%). TLC (30% ethyl acetate in hexane) Rf=0.52; LCMS: RtH7=1.487; [M+1]+=344.0 and 346.0; HPLC RtH9=7.6 min (74%); 1H NMR (300 MHz, CDCl3): b 8.41-8.34 (t, 1H), 7.54 (s, 1H), 7.32-7.28 (m, 1H), 4.51 (dd, 2H), 4.27-4.21 (q, 4H), 1.45 (s, 3H), 1.39 (s, 3H), 1.23 (t, 3H).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to rt
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washby washing with water, brine
  6. customby drying over anhy
  7. concentrationOrganic layer was concentrated under reduced pressure
  8. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-95e3b50fde864913bd2a69cdf36da704
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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