Ethyl Acetate → HCID 57667019, compound

HRID 600854Notes

Reaction equation

HRID 600854 reaction equation
[NH2:1][C@@H:2]([CH2:5][N:6]([CH2:17][CH3:18])[C:7]1[CH:8]=[N:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=1)[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:25]#[C:26]Br.C(OC(=O)C)C>C1COCC1.O>[NH2:25][C:26]1[O:4][CH2:3][C@H:2]([CH2:5][N:6]([CH2:17][CH3:18])[C:7]2[CH:8]=[N:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=2)[N:1]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 67271061HCID 67271061, compound

Product 1

HCID 57667019HCID 57667019, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of (S)-2-amino-3-[ethyl-(6-trifluoromethyl-pyridin-3-yl)-amino]-propan-1-ol (0.04 g, 0.15 mmol) and K2CO3 (0.025 g, 0.18 mmol) in THF (2 ml) under an argon atmosphere was added a solution of cyanogen bromide (0.025 g, 0.18 mmol) in THF (1 ml). The mixture was stirred for 1 hour, then ethylacetate and water were added. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, EtOAc/MeOH=9:1) to give the title compound as white solid (0.02 g, 46%), MS (ISP): 289.0 ([M+H]+).

Workup

  1. extractionThe aqueous phase was back extracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (SiO2, EtOAc/MeOH=9:1)

Sources & evidence

ORD record
ord-1bce10b6708649f791df1f5ac87fba62
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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