Sodium Hydroxide → HCID 178520498, compound

HRID 1480410Notes

Reaction equation

HRID 1480410 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([NH:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:10])[O:4][N:3]=1.[OH-].[Na+].[C:22](Cl)(=[O:33])[O:23][CH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=1>C(Cl)Cl>[OH:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([NH:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:22]([O:23][CH2:24][C:25]3[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=3)=[O:33])[CH2:18][CH2:19]2)=[O:10])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 178520497HCID 178520497, compound

Product 1

HCID 178520498HCID 178520498, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3-(3-Hydroxyisoxazol-5-yl)-N-(2-(piperidin-4-yl)ethyl)propanamide (step 2) (201 mg, 0.662 mmol) was suspended in DCM (2 ml). 2M NaOH (1 ml, 2.00 mmol) was added and the reaction mixture stirred. To the mixture was added a solution of 3,5-dichlorobenzyl carbonochloridate (158 mg, 0.662 mmol) in DCM (1 ml) and the reaction mixture was stirred vigorously overnight. The resulting mixture was diluted with DCM and washed with citric acid. The organics were separated and evaporated under reduced pressure. The crude residue was dissolved in DMSO and purified by preparative HPLC. The product fractions were concentrated under reduced pressure and partitioned between EtOAc and water. The organics were separated, dried over MgSO4 (anh) filtered and evaporated under reduced pressure and dried in a high vacuum oven to afford the title compound;

Workup

  1. stirringthe reaction mixture was stirred vigorously overnight
  2. washwashed with citric acid
  3. customThe organics were separated
  4. customevaporated under reduced pressure
  5. dissolutionThe crude residue was dissolved in DMSO
  6. custompurified by preparative HPLC
  7. concentrationThe product fractions were concentrated under reduced pressure
  8. custompartitioned between EtOAc and water
  9. customThe organics were separated
  10. dry with materialdried over MgSO4 (anh)
  11. filtrationfiltered
  12. customevaporated under reduced pressure
  13. customdried in a high vacuum oven

Sources & evidence

ORD record
ord-2a4091af24234cc5a39d29afede977b8
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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