Hydrochloric Acid → HCID 49848067, compound

HRID 389865Notes

Reaction equation

HRID 389865 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:18]([S:21](Cl)(=[O:23])=[O:22])[CH2:19][CH3:20].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:16][CH2:15][N:14]2[S:21]([CH2:18][CH2:19][CH3:20])(=[O:23])=[O:22])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67953688HCID 67953688, compound

Product 1

HCID 49848067HCID 49848067, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-Azetidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (100 mg; 0.385 mmol) in DMF (1 mL) is added n-propylsulfonyl chloride (0.043 mL; 0.385 mmol) and N,N-diisopropylethylamine (0.201 mL; 1.155 mmol). The reaction mixture is left stirring at room temperature for 18 hours. After this time, the reaction mixture is diluted with ethyl acetate and washed with water twice then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/hexanes provides the title compound, m/z 330 [M+H+].

Workup

  1. waitThe reaction mixture is left
  2. washwashed with water twice
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-398eb9c5a46a4a3787dafc55c64b7a52
Source dataset
uspto-grants-2013_02
Patent number
US08383615B2

Reaction notes

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