Methanesulfonyl chloride → HCID 46873103, compound

HRID 336192Notes

Reaction equation

HRID 336192 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].[CH3:27][S:28](Cl)(=[O:30])=[O: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]([S:28]([CH3:27])(=[O:30])=[O:29])[CH2:23][CH2:22]2)=[O:20])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70864988HCID 70864988, compound

Product 1

HCID 46873103HCID 46873103, 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 methane sulfonyl chloride (0.013 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 442 [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-7f1f2eefe4214fe68b7428db2bccc0f7
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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