Pyridine → 620627-47-6

HRID 1247764Notes

Reaction equation

HRID 1247764 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-53f2a83448b942aab60d991a2c572bc7
Source dataset
uspto-grants-2006_10
Patent number
US07129378B2

Reaction notes

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