Hydrogen Bromide → HCID 21193040, compound

HRID 1068188Notes

Reaction equation

HRID 1068188 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N+](=C)=[N-].Br.[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH:26]([C:27](=[S:29])[NH2:28])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CCO>[CH2:4]([C:3]1[S:29][C:27]([CH:26]2[CH2:30][CH2:31][N:23]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:24][CH2:25]2)=[N:28][CH:2]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 9550DiazomethaneHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 114699271-bromo-3-phenyl-2-propanone

Product 1

HCID 21193040HCID 21193040, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 65 mg of 1-bromo-3-phenyl-2-propanone (from reacting the acid chloride with diazomethane followed by hydrogen bromide) in 4 ml EtOH was added 74 mg of 1-boc-isonipecot-thioamide (from Step A). The reaction was stirred for 2 hours at 80° C. The solvent was then evaporated under reduced pressure. The residue was purified by flash chromatography with 10% EtOAc in hexane to give 37 mg of the title compound.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-7528e78b9d624afa874fddc9ecb57700
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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