Methanol → HCID 54591596, compound

HRID 509253Notes

Reaction equation

HRID 509253 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[N:19]=[C:18]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[CH:17]=[CH:16][CH:15]=1)=[O:13])[CH2:8]2.CO>FC(F)(F)C(O)=O>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:13])[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[N:19]=1)[CH2:8]2

Participants

4

Reactant 2

HCID 887MethanolHCID 67466816HCID 67466816, compound

Product 1

HCID 54591596HCID 54591596, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

After tert-butyl 4-(6-(adamantan-2-ylcarbamoyl)pyridin-2-yl)piperazine-1-carboxylate (86 mg, 0.195 mmol) was dissolved in MC (2 ml), trifluoroacetic acid (2 ml) was added thereto, and then the resulting mixture was stirred at room temperature under nitrogen stream for 4 hours. The resulting reaction liquid was concentrated under reduced pressure, followed by addition of a saturated aqueous NaHCO3 solution (10 ml), and then extracted with MC (15 ml×2). The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (10% MeOH/MC), to obtain 65 mg of colorless oil (98%). MS (ESI): 341 [M+H]+

Workup

  1. additionwas added
  2. customThe resulting reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. additionfollowed by addition of a saturated aqueous NaHCO3 solution (10 ml)
  5. extractionextracted with MC (15 ml×2)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfollowed by filtration and concentration
  8. customthe residue thus obtained

Sources & evidence

ORD record
ord-1289857af7d740c1ba3ec2b6d9ece247
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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