Hydrochloric Acid → HCID 67456434, compound

HRID 469735Notes

Reaction equation

HRID 469735 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C)C=O.O>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:26]([C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 67455816(S)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Product 1

HCID 67456434HCID 67456434, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (0.150 g; 0.580 mmol) in N,N-dimethylformamide (2 mL) is added 4-chlorophenylsulfonyl chloride (0.122 g; 0.580 mmol) and triethylamine (0.243 mL; 1.740 mmol). The mixture is stirred at room temperature overnight. After this time, the mixture is diluted with water and extracted with ethyl acetate. The combined organics are washed with aqueous saturated sodium bicarbonate solution, 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 412 [M+NH4]+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics are washed with aqueous saturated sodium bicarbonate solution, 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-7c2d31c298a04bc99acc7a52626b422e
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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