N-(2-hydroxy-2-phenylethyl)pent-4-ynamide → Pent-4-ynoic acid (2-oxo-2-phenyl-ethyl)-amide

HRID 1189091Notes

Reaction equation

HRID 1189091 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][NH:4][C:5](=[O:10])[CH2:6][CH2:7][C:8]#[CH:9].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[C:2]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:3][NH:4][C:5](=[O:10])[CH2:6][CH2:7][C:8]#[CH:9]

Participants

4

Reactant 2

HCID 86086915N-(2-hydroxy-2-phenylethyl)pent-4-ynamideHCID 178418287HCID 178418287, compound

Product 1

HCID 86086916Pent-4-ynoic acid (2-oxo-2-phenyl-ethyl)-amideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

169 mg (0.78 mmol) of N-(2-hydroxy-2-phenylethyl)pent-4-ynamide in DCM (1 mL) were added to a solution of PCC (326 mg, 1.48 mmol) in DCM (4 mL). The reaction mixture was stirred for 4 hours at room temperature, dissolved in DCM and then quenched with NaOH 1N. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to yield 160 mg (0.74 mmol, 95%) of pent-4-ynoic acid (2-oxo-2-phenyl-ethyl)-amide as a yellow solid.

Workup

  1. customquenched with NaOH 1N
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d3c2dbf7501c4a2db9fc40356b048767
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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