Sodium Hydroxide → 3-Chloro-5-fluorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate

HRID 1480441Notes

Reaction equation

HRID 1480441 reaction equation
[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:25])[NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:26](=O)([O:37]N1C(=O)CCC1=O)[O:27][CH2:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([Cl:36])[CH:30]=1.[OH-].[Na+]>C(Cl)Cl>[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:18][CH:19]2[CH2:20][CH2:21][N:22]([C:26]([O:27][CH2:28][C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([Cl:36])[CH:30]=3)=[O:37])[CH2:23][CH2:24]2)=[O:25])[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 86722666HCID 86722666, compoundHCID 867226683-Chloro-5-fluorobenzyl 2,5-dioxopyrrolidin-1-yl carbonate

Product 1

HCID 867226673-Chloro-5-fluorobenzyl 4-(4-(1-((pivaloyloxy)methyl)-1H-1,2,3-triazol-4-yl)butanamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of (4-(4-oxo-4-(piperidin-4-ylamino)butyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (step 5) (150 mg, 0.387 mmol) and 3-chloro-5-fluorobenzyl 2,5-dioxopyrrolidin-1-yl carbonate (117 mg, 0.387 mmol) in DCM (5 mL) was added NaOH (1.547 mL, 1.547 mmol) with stirring at RT and the mixture was stirred at RT for 18 hrs. A further 5 ml DCM was added followed by 1M NaOH (1 ml). The reaction mixture was diluted with DCM (30 ml) and the organic portion was dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product;

Workup

  1. stirringthe mixture was stirred at RT for 18 hrs
  2. dry with materialthe organic portion was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7123f637e6a049abad14d7391e2f9447
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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