Water → HCID 178516682, compound

HRID 1672737Notes

Reaction equation

HRID 1672737 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-:18].O.[CH2:20]([O:27][C:28]1[CH:51]=[C:50]([Cl:52])[C:31]([CH2:32][C@@H:33]2[CH2:37][CH2:36][N:35]([C@H:38]3[CH2:43][CH2:42][C@H:41](OS(C)(=O)=O)[CH2:40][CH2:39]3)[C:34]2=[O:49])=[C:30]([Cl:53])[CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[CH2:20]([O:27][C:28]1[CH:51]=[C:50]([Cl:52])[C:31]([CH2:32][C@@H:33]2[CH2:37][CH2:36][N:35]([C@H:38]3[CH2:43][CH2:42][C@@H:41]([F:18])[CH2:40][CH2:39]3)[C:34]2=[O:49])=[C:30]([Cl:53])[CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 178505322HCID 178505322, compound

Product 1

HCID 178516682HCID 178516682, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve TBAF.3H2O (1.595 g, 1.30 mmol) in 10 ml of acetonitrile. Add water (0.18 ml, 9.91 mmol) and stir for 10 minutes. Add (R)-trans-Methanesulfonic acid 4-[3-(4-benzyloxy-2,6-dichloro-benzyl)-2-oxo-pyrrolidin-1-yl]-cyclohexyl ester (Preparation 14) (1.30 g, 2.48 mmol). Stir at 80° C. for 12 hours. Quench with saturated NaHCO3 and extract with ethyl acetate. Wash the extract with brine. Dry over magnesium sulfate, filter, and concentrate. After flash column chromatography receive 0.230 g (21%) of the title compound: Mass spectrum (apci) m/z=450 (M+H).

Workup

  1. customQuench with saturated NaHCO3
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-9f32015a8c9e41838bccc07a95c9e54e
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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