Hydrochloric Acid → HCID 178520557, compound

HRID 1480471Notes

Reaction equation

HRID 1480471 reaction equation
C(OC[N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[O:27])[CH2:22][CH2:21]2)=[O:18])[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+].Cl>CO>[NH:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=3[Cl:37])=[O:27])[CH2:22][CH2:21]2)=[O:18])[N:11]=[N:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86722692HCID 86722692, compound

Product 1

HCID 178520557HCID 178520557, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2,4-dichlorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate (100 mg, 0.180 mmol) in MeOH (1 mL) at RT was added 1M NaOH (0.397 mL, 0.397 mmol). The reaction mixture was allowed to stir for 1 hr. An equivalent of 1M HCl (0.4 ml) was added to neutralise the reaction mixture and the MeOH removed under reduced pressure. The reaction mixture was diluted with EtOAc and water and the organic portion was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Trituration with diethyl ether afforded the title product;

Workup

  1. customthe MeOH removed under reduced pressure
  2. additionThe reaction mixture was diluted with EtOAc and water
  3. customthe organic portion was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3006bc62710471088f33a5b8e4072b3
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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