Hydrochloric Acid → HCID 178520496, compound

HRID 1480430Notes

Reaction equation

HRID 1480430 reaction equation
[C:1](Cl)(=[O:12])[O:2][CH2:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[CH:5]=1.[OH:14][C:15]1[CH:19]=[C:18]([CH2:20][CH2:21][C:22]([NH:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:23])[O:17][N:16]=1.[OH-].[Na+].Cl>C(Cl)Cl.CCOC(C)=O>[OH:14][C:15]1[CH:19]=[C:18]([CH2:20][CH2:21][C:22]([NH:24][CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([C:1]([O:2][CH2:3][C:4]3[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[CH:5]=3)=[O:12])[CH2:30][CH2:31]2)=[O:23])[O:17][N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 178520495HCID 178520495, compound

Product 1

HCID 178520496HCID 178520496, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3,5-dichlorobenzyl carbonochloridate (331 mg, 1.380 mmol) and 3-(3-hydroxyisoxazol-5-yl)-N-(piperidin-4-ylmethyl)propanamide (step 2) (200 mg, 0.690 mmol) in DCM (7 ml) was added 2M NaOH solution (6.90 ml, 13.80 mmol) and the mixture stirred vigorously at RT for 16 hrs. The mixture was diluted with EtOAc (50 ml) and acidified with 2M HCl. The organics were dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in MeOH/EtOAc and dry loaded onto silica (10 g). This was applied to a 12 g silica cartridge, eluting with 1% AcOH/EtOAc. The product fractions were combined and concentrated under reduced pressure and the residue was triturated with diethyl ether to afford 3,5-dichlorobenzyl 4-((3-(3-hydroxyisoxazol-5-yl)propanamido)methyl)piperidine-1-carboxylate as a white solid.

Workup

  1. dry with materialThe organics were dried (MgSO4)
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in MeOH/EtOAc
  4. customdry
  5. washeluting with 1% AcOH/EtOAc
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-46e72781058e48ed8b90ff532850af03
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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