Triphosgene → HCID 118353903, compound

HRID 590561Notes

Reaction equation

HRID 590561 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:18][NH2:19])[NH:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)=[O:4].Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl.CCN(C(C)C)C(C)C>[O:23]=[C:21]1[N:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:18][NH:19]1

Participants

5

Reactant 2

HCID 94429TriphosgeneHCID 118353963HCID 118353963, compound

Product 1

HCID 118353903HCID 118353903, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

3-Aminomethyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (Compound AA) from Step 3 was dissolved in 4 mL of dichloromethane and 1 mL of DIPEA, then triphosgene (108 mg, 0.36 mmol) was added at room temperature. After the reaction mixture was stirred for 30 minutes, the solvent was removed in vacuo. The residue was dissolved in 3 mL of dichloromethane and 1 mL of TFA. The reaction mixture was stirred for 1 hour at room temperature, and the solvent was removed in vacuo to give the crude Compound X which was used directly without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 3 mL of dichloromethane
  3. stirringThe reaction mixture was stirred for 1 hour at room temperature
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1eff2de6c79e4007bec6efea80e8caa2
Source dataset
uspto-grants-2016_01
Patent number
US09233978B2

Reaction notes

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