Triethylamine → HCID 68711938, compound

HRID 1927797Notes

Reaction equation

HRID 1927797 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([NH2:23])=O)=[O:15])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]#[N:23])=[O:15])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 9845Trifluoroacetic anhydrideHCID 68709601HCID 68709601, compound

Product 1

HCID 68711938HCID 68711938, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(2S)-1-(2-(N-tert-Butyloxycarbonyl-N-(2-methylpropyl)amino)acetyl)pyrrolidine-2-carboxamide (330 mg, 1.01 mmol) was dissolved in dry THF (20 ml). The solution was cooled to 0° C., triethylamine (210 mg, 2.1 mmol) was added followed by the slow addition of trifluoroacetic anhydride (460 g, 2.2 mmol). The pH was adjusted to pH9 with triethylamine. After 30 min the reaction mixture was diluted with ethyl acetate (100 ml), washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 3% methanol, 97% chloroform) to give an orange oil identified as the title compound (156 mg, 0.50 mmol, 50%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography (eluant: 3% methanol, 97% chloroform)
  5. customto give an orange oil

Sources & evidence

ORD record
ord-5457260f24f94c2bb0bd8de5074efb37
Source dataset
uspto-grants-2012_05
Patent number
US08183280B2

Reaction notes

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