Propionyl chloride → HCID 46873105, compound

HRID 336193Notes

Reaction equation

HRID 336193 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:27](Cl)(=[O:30])[CH2:28][CH3:29].C(N(CC)C(C)C)(C)C>C1COCC1.C(OCC)(=O)C.O>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2[C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:23][CH2:22]2)=[O:20])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 70864988HCID 70864988, compound

Product 1

HCID 46873105HCID 46873105, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-(piperazine-1-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (60 mg; 0.165 mmol) in THF (1 mL) is added propionyl chloride (0.015 mL; 0.17 mmol), followed by N,N-diisopropylethylamine (0.03 mL; 0.17 mmol). The mixture is stirred at room temperature for 18 hours. The mixture is diluted with ethyl acetate and water. The layers are separated and the organic layer is concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/Hexanes provides the title compound, m/z 420 [M+H+].

Workup

  1. customThe layers are separated
  2. concentrationthe organic layer is concentrated in vacuo
  3. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1118004190e14d9094518a3ab9334895
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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