Water → HCID 57453597, compound

HRID 639758Notes

Reaction equation

HRID 639758 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-5abd87167e4a40cf88a66f7d5690dca9
Source dataset
uspto-grants-2010_04
Patent number
US07691888B2

Reaction notes

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