Acetyl chloride → HCID 121410336, compound

HRID 59791Notes

Reaction equation

HRID 59791 reaction equation
[Br:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](=[O:32])(=[O:31])[NH2:30])=[CH:25][CH:24]=2)[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:37](Cl)(=[O:39])[CH3:38]>C1COCC1>[C:37]([NH:30][S:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:8]([CH2:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:34][CH:33]=2)[CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[CH:28][CH:27]=1)(=[O:32])=[O:31])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 121410344HCID 121410344, compound

Product 1

HCID 121410336HCID 121410336, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-((4-bromophenethyl)(4-sulfamoylbenzyl)amino)piperidine-1-carboxylate (see Example 15, step 1) was dissolved in anhydrous THF (5 mL/mmol) under atmosphere of argon and the solution was cooled to 0° C. Sodium hydride (2 equiv) was then added in one portion and after 10 minutes acetyl chloride (2 equiv) was added dropwise by syringe over 10 minutes. The cooling batch was removed and the reaction mixture was allowed to stir for two days after which time the starting material could no longer be detected. The reaction mixture was then diluted with EtOAc (12 mL/mmol of starting material), washed with 1 M NaOH (2×), water (2×) and brine (2×) and dried over anhydrous MgSO4. After filtration of the drying agent the solvent was stripped off and the crude product was purified by column chromatography (yield 65%).

Workup

  1. additionwas added dropwise by syringe over 10 minutes
  2. customThe cooling batch was removed
  3. additionThe reaction mixture was then diluted with EtOAc (12 mL/mmol of starting material)
  4. washwashed with 1 M NaOH (2×), water (2×) and brine (2×)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationAfter filtration of the drying agent the solvent
  7. customthe crude product was purified by column chromatography (yield 65%)

Sources & evidence

ORD record
ord-973ab5608a3e4c39a2da2231525f4966
Source dataset
uspto-grants-2016_09
Patent number
US09440953B2

Reaction notes

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