Dimethyl Sulfide → HCID 69652385, compound

HRID 2212210Notes

Reaction equation

HRID 2212210 reaction equation
S(C)C.[C:4]([O:8][C:9]([N:11]1[CH2:16][CH:15]([N:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:27])[C:21]=3[C:20]3=[N:28][O:29][C:30]([CH3:31])=[C:19]3[C:18]2=[O:32])[CH2:14][CH:13]([C:33](O)=[O:34])[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C1COCC1>[C:4]([O:8][C:9]([N:11]1[CH2:12][CH:13]([CH2:33][OH:34])[CH2:14][CH:15]([N:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:27])[C:21]=3[C:20]3=[N:28][O:29][C:30]([CH3:31])=[C:19]3[C:18]2=[O:32])[CH2:16]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 69652404HCID 69652404, compound

Product 1

HCID 69652385HCID 69652385, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add BH3.SMe2 (3.2 mL, 6.4 mmol, 2.0 M in THF) to a solution of 5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (1.5 g, 3.2 mmol) in THF (20 mL) at 0° C. Remove the ice bath and stir for 30 min. Quench dropwise with MeOH and concentrate to dryness. Partition between 20% iPrOH/CHCl3 and water. Wash 2× sat. aq NaHCO3, wash 2× brine, dry over Na2SO4, filter and concentrate to dryness. Purify by radial chromatography using MeOH/CHCl3 as eluant and concentrate to dryness to afford the title compound (0.95 g, 66%) as a white foam as a mixture of cis isomers. MS(IS) 448.2 (M+); HPLC (40% IPA 60% heptane on a Chiralpak AD (0.46×25 cm) 1.5 mL/min flow; 25 μL Inj.; 225 nM) Rt=3.28 min (72.1%), 4.48 min (27.8%).

Workup

  1. additionAdd BH3
  2. customat 0° C
  3. customRemove the ice bath
  4. customQuench dropwise with MeOH
  5. concentrationconcentrate to dryness
  6. customPartition between 20% iPrOH/CHCl3 and water
  7. washWash 2× sat. aq NaHCO3
  8. washwash 2× brine
  9. dry with materialdry over Na2SO4
  10. filtrationfilter
  11. concentrationconcentrate to dryness
  12. customPurify by radial chromatography
  13. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-50552ccbcca44260bc878601693c365f
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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