Triethylamine → (R)-methyl 2-(2-nitropyridin-3-ylamino)pent-4-ynoate

HRID 1432028Notes

Reaction equation

HRID 1432028 reaction equation
F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:11][C@H:12]([CH2:17][C:18]#[CH:19])[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C>CN(C=O)C>[N+:8]([C:3]1[C:2]([NH:11][C@H:12]([CH2:17][C:18]#[CH:19])[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=[CH:5][N:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27628023-Fluoro-2-nitropyridineHCID 44205355(R)-2-Amino-4-pentynoic acid, methyl ester

Product 1

HCID 86604879(R)-methyl 2-(2-nitropyridin-3-ylamino)pent-4-ynoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-fluoro-2-nitropyridine (860 mg, 6.05 mmol) and (R)-methyl 2-aminopent-4-ynoate (1.924 g, 15.131 mmol) in DMF was added triethylamine (2.55 ml, 18.16 mmol) and the resulting solution was stirred over the weekend. The reaction mixture was quenched with sat. NaHCO3, extracted with EtOAc/hexane=2:1, washed with brine, dried over Na2SO4 and the solvent was evaporated. Flash chromatography (SiO2, DCM to DCM/EtOAc=3:1 to 2:1) afforded the title compound as a pale yellow solid.

Workup

  1. customThe reaction mixture was quenched with sat. NaHCO3
  2. extractionextracted with EtOAc/hexane=2:1
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d2c9b7f363894969b9c62bc7ba9078e8
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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