Propionitrile → HCID 66771118, compound

HRID 1025326Notes

Reaction equation

HRID 1025326 reaction equation
[N+](C1C=C(S(O[C@@H:14]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]2)(=O)=O)C=CC=1)([O-])=O.C(#N)CC.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[SH:41].C(N(CC)CC)C>C([O-])([O-])=O.[Na+].[Na+]>[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[S:41][C@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]1

Participants

6

Reactant 4

HCID 7854PropionitrileHCID 8471TriethylamineHCID 80599o-ChlorothiophenolHCID 86646817HCID 86646817, compound

Product 1

HCID 66771118HCID 66771118, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

Under an atmosphere of argon, (2S,4S)-1-tert-butyl 2-methyl 4-(3-nitrophenylsulfonyloxy)pyrrolidine-1,2-dicarboxylate (8.5 g, 19.7 mmol, Eq: 1.00) was combined with propionitrile (82.0 ml) to give a light brown solution. Then 2-chlorobenzenethiol (4.28 g, 3.38 ml, 29.6 mmol, Eq: 1.50) and triethylamine (4.00 g, 5.5 ml, 39.5 mmol, Eq: 2.00) were added dropwise. The reaction was stirred overnight at reflux (100° C.). The reaction was cooled to room temperature, and poured in 50 ml Na2CO3 solution (10%), and extracted with 2×100 ml ethyl acetate. The organic layers were washed with 50 ml HCl 0.1M and 50 ml satd. NaCl solution. The organic layer was stirred over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (70 g column, from 100% to 80% heptane in ethyl acetate). The title compound was obtained as a yellow oil (5.7 g, 77.6%, MS (m/e)=372.1 [M+H+]).

Workup

  1. customto give a light brown solution
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with 2×100 ml ethyl acetate
  4. washThe organic layers were washed with 50 ml HCl 0.1M and 50 ml
  5. stirringThe organic layer was stirred over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (70 g column, from 100% to 80% heptane in ethyl acetate)

Sources & evidence

ORD record
ord-6f2bfb9600a74525b221206813b0f448
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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