Hydrochloric Acid → HCID 178520560, compound

HRID 1480442Notes

Reaction equation

HRID 1480442 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]=[C:34]([F:36])[CH:33]=[C:32]([Cl:37])[CH:31]=3)=[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]=[C:34]([F:36])[CH:33]=[C:32]([Cl:37])[CH:31]=3)=[O:27])[CH2:22][CH2:21]2)=[O:18])[N:11]=[N:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867226673-Chloro-5-fluorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate

Product 1

HCID 178520560HCID 178520560, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-chloro-5-fluorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate (200 mg, 0.372 mmol) in MeOH (1 mL) was added 1M NaOH (0.818 mL, 0.818 mmol). The reaction mixture was allowed to stir at RT for 1 hour. An equivalent of 1M HCl (0.8 ml) was added to neutralise the reaction mixture and the MeOH was removed under reduced pressure. The mixture was diluted with water and extracted with EtOAc. The organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-100% EtOAc in hexanes and then 0-10% MeOH in EtOAc to afford the title product;

Workup

  1. customthe MeOH was removed under reduced pressure
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-586b64d5925948c68c54906c087ebfb2
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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