2,3-Dichlorobenzoic acid → tert-butyl (1S,4S)-5-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 421991Notes

Reaction equation

HRID 421991 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].ON1C2C=CC=CC=2N=N1.[Cl:25][C:26]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](O)=[O:29]>C(Cl)(Cl)Cl>[Cl:25][C:26]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:27]=1[C:28]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:29]

Participants

5

Reactant 3

HCID 57652,3-Dichlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 66676957tert-butyl (1S,4S)-5-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 3.0 g of tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, 3.2 g of 1-(3-dimethyl-aminopropyl) -3-ethylcarbodiimide hydrochloride, 2.6 g of 1-hydroxybenzotriazole, 2.9 g of 2,3-dichlorobenzoic acid and 60 ml of chloroform was stirred at room temperature for 17 hours and then diluted with chloroform. An insoluble matter was filtered off using Celite and the resulting mixture was washed with water with saturated brine. The resulting organic layer was dried over magnesium sulfate and filtered, the filtrate was concentrated in vacuo and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 1/1) to give the title compound.

Workup

  1. filtrationAn insoluble matter was filtered off
  2. washthe resulting mixture was washed with water with saturated brine
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=9/1 to 1/1)

Sources & evidence

ORD record
ord-383027df1df34715a8ea125cd65e622a
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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