Triethylamine → HCID 24805217, compound

HRID 1927798Notes

Reaction equation

HRID 1927798 reaction equation
C(O[C:6]([N:8]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:22])=[O:15])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])(C)(C)C.C(N(CC)CC)C.C(Cl)(=O)[C:31]1[C:32]([O:37][CH3:38])=[CH:33][CH:34]=[CH:35][CH:36]=1>FC(F)(F)C(O)=O>[CH3:38][O:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:6]([N:8]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:22])=[O:15])[CH2:9][CH:10]([CH3:11])[CH3:12])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 68711938HCID 68711938, compound

Product 1

HCID 24805217HCID 24805217, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

(2S)-1-(2-(N-tert-Butyloxycarbonyl-N-(2-methylpropyl)amino)acetyl)pyrrolidine-2-carbonitrile (25 mg, 0.081 mmol) was treated with trifluoroacetic acid (50 ml). After 1 h at room temperature the solvent was removed in vacuo and the residue dissolved in CH2Cl2 (100 ml). The solution was cooled to 0° C., triethylamine (30 mg, 0.3 mmol) was added followed by 2-anisoyl chloride (15 mg, 0.088 mmol). After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue dissolved in ethyl acetate (200 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 2% methanol, 98% chloroform) to give a colourless oil identified as the title compound (18 mg, 0.052 mmol, 66%).

Workup

  1. customAfter 1 h at room temperature the solvent was removed in vacuo
  2. dissolutionthe residue dissolved in CH2Cl2 (100 ml)
  3. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate (200 ml)
  5. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (eluant: 2% methanol, 98% chloroform)
  9. customto give a colourless oil

Sources & evidence

ORD record
ord-1d9f13dff1094bde955b4b8d65eaf446
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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