Water → HCID 57453597, compound

HRID 222606Notes

Reaction equation

HRID 222606 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(OC([NH:20][NH2:21])=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[NH:20]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[NH2:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70091tert-Butyl carbazateHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 57453597HCID 57453597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3 g of methyl 3-bromomethylbenzoate (13 mmol), 2.6 g of tert-butoxycarbonylhydrazine (19 mmol) and 3.1 g of potassium carbonate (23 mmol) in 30 ml of DMF is stirred at RT for 24 h. After water has been added, the reaction mixture is extracted with dichloromethane. The organic phase is dried, filtered and evaporated, and the residue is purified chromatographically. The BOC protecting group is then eliminated using 30 ml of hydrochloric acid (4 M in dioxane). Yield: 1.25 g

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue is purified chromatographically

Sources & evidence

ORD record
ord-9ed62425ed3c4ed5b2dcea735cdd27b2
Source dataset
uspto-grants-2012_06
Patent number
US08207349B2

Reaction notes

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