Hydrochloric Acid → HCID 67458256, compound

HRID 469720Notes

Reaction equation

HRID 469720 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[N:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:25]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:26])=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 67457204HCID 67457204, compound

Product 1

HCID 67458256HCID 67458256, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)-amide; hydrochloride (0.2 g; 0.731 mmol) in N,N-dimethylformamide (2 mL) is added morpholine carbonylchloride (0.084 mL; 0.731 mmol) and N,N-diisopropylethylamine (0.267 mL; 1.535 mmol) and the reaction mixture stirred overnight at room temperature. After this time, the mixture is diluted with water and extracted with ethyl acetate. The combined organics are washed with 1N hydrochloric acid and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude material is purified by preparative HPLC to afford title compound. ESI m/z 351 [M+H]+/349 [M−H]−

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics are washed with 1N hydrochloric acid and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material is purified by preparative HPLC

Sources & evidence

ORD record
ord-eb3b64da53e6497f8f80518c3a3f22e2
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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