Pyridine → 620627-47-6

HRID 2055885Notes

Reaction equation

HRID 2055885 reaction equation
[OH:1][C:2]([CH3:22])([CH3:21])[C@H:3]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:23]=[S:24](Cl)Cl.N1C=CC=CC=1>C1COCC1>[CH3:21][C:2]1([CH3:22])[O:1][S@:24](=[O:23])[N:10]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[C@@H:3]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 26596944N-[(1R)-2-Hydroxy-2-methyl-1-phenylpropyl]-4-methylbenzene-1-sulfonamide

Product 1

HCID 57351597620627-47-6Yield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (1R)-N-(2-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzene sulfonamide (2.0 g, 6.3 mmol) in THF 8 mL at −45° C. was added SOCl2 (1.12 g, 9.4 mmol), followed by slow addition of pyridine (1.24 g, 12.9 mmol) in THF (8 mL) over a period of 2 h. The reaction was monitored on TLC. The reaction was quenched by addition of saturated aqueous NaHCO3 and the mixture was extracted with EtOAc (30 ml), and organic phase washed with brine (20 mL) and evaporated to dryness. The residue was added hexane (40 mL) and stirred at ambient for 2 h. The precipitate formed was filtered and wet cake washed with hexane to afford the title compound (2.0 g, 87.5%) with 99% de.

Workup

  1. customThe reaction was quenched by addition of saturated aqueous NaHCO3
  2. extractionthe mixture was extracted with EtOAc (30 ml), and organic phase
  3. washwashed with brine (20 mL)
  4. customevaporated to dryness
  5. additionThe residue was added hexane (40 mL)
  6. customThe precipitate formed
  7. filtrationwas filtered
  8. washwet cake washed with hexane

Sources & evidence

ORD record
ord-822786cec9ee4b86a18251d1bf491e1f
Source dataset
uspto-grants-2008_02
Patent number
US07332610B2

Reaction notes

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