Triethylamine → HCID 18659854, compound

HRID 1291771Notes

Reaction equation

HRID 1291771 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].C(N(CC)CC)C.[C:17]1([CH2:23][C@H:24]([NH2:27])[CH:25]=[CH2:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[CH3:1][S:2]([NH:27][C@H:24]([CH:25]=[CH2:26])[CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 10034765HCID 10034765, compound

Product 1

HCID 18659854HCID 18659854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.36 g (13.6 mmol) of methansulfonic acid anhydride and 1.88 ml (13.6 mmol) of triethylamine are added at 0° C. to a solution of 1 g (6.8 mmol) of 1-phenyl-3-buten-2(S)-amine from Example 16b) in 10 ml methylene chloride and the mixture is stirred for 1 h. The reaction mixture is washed with water and saturated sodium hydrogen carbonate solution and the organic phase is filtered through cotton wadding and concentrated by evaporation to yield 2(S)-methylsulfonylamino-1-phenyl-3-butene. 1 g (4.4 mmol) of that crude product is dissolved in 30 ml of methylene chloride, 3.05 g (17.7 mmol) of 4-chloroperbenzoic acid are added at RT and stirring is carried out for 18 h. The reaction solution is washed 5 times with 10% aqueous sodium sulfite solution, filtered through cotton wadding and fully concentrated by evaporation. According to 1H-NMR the crude product contains both the (2R)- and the (2S)-epimer in a ratio of 4:1. 1 H-NMR (200 MHz, CD3OD): 2.30 and 2.52 (2 s, together 3H), 2.6 to 3.2 (m, 5H), 3.55 (m, 1H) 7.32 (m, 5H).

Workup

  1. washThe reaction mixture is washed with water and saturated sodium hydrogen carbonate solution
  2. filtrationthe organic phase is filtered through cotton wadding
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-729f1d77316740bdb6b4e13a403e5368
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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