Methanesulfonyl chloride → HCID 15378782, compound

HRID 1386833Notes

Reaction equation

HRID 1386833 reaction equation
C(N(C(C)C)CC)(C)C.[N+:10]([C:13]1[CH:14]=[C:15]([C@@H:19]([OH:22])[CH2:20][CH3:21])[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[S:24]([O:22][C@H:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1)[CH2:20][CH3:21])(=[O:26])(=[O:25])[CH3:23]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 10773741(S)-1-(3-Nitrophenyl)propan-1-ol

Product 1

HCID 15378782HCID 15378782, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Diisopropylethylamine (1.07 g, 8.3 mmol) is added to a mixture of (S)-1-(3-nitrophenyl)propanol (XXI, PREPARATION 1, 1 g, 5.5 mmol) in methylene chloride (20 mL). The mixture is cooled to −20° and methanesulfonyl chloride (0.69 g, 6.02 mmol) is added. The reaction is held at −20° for 10 min, then held at 0° for 40 min. The reaction is diluted with methylene chloride, sodium bicarbonate (5%) is added and the phases are separated. The methylene chloride is evaporated to give the title compound, [α]D=−79.9° (ethanol, c=1); TLC (silica gel GF, ethyl acetate/hexane, 20/80) Rf=0.19; NMR (CDCl3, TMS) 0.96-1.01, 1.88-2.17, 2.89, 5.54-5.59, 7.57-7.62, 7.70-7.73 and 8.20-8.24 δ.

Workup

  1. temperatureThe mixture is cooled to −20°
  2. waitheld at 0° for 40 min
  3. additionis added
  4. customthe phases are separated
  5. customThe methylene chloride is evaporated

Sources & evidence

ORD record
ord-94a83c3f87c44da79d46bf6804c7acb1
Source dataset
uspto-grants-2001_07
Patent number
US06265604B1

Reaction notes

Loading…