Triphosgene → HCID 68713012, compound

HRID 2069317Notes

Reaction equation

HRID 2069317 reaction equation
[C:1]1([NH:7][NH:8][C:9]([C@H:11]2[CH2:13][C@H:12]2[C:14]([OH:16])=[O:15])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[O:20]=[C:18]1[O:10][C:9]([C@H:11]2[CH2:13][C@H:12]2[C:14]([OH:16])=[O:15])=[N:8][N:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 68708522HCID 68708522, compound

Product 1

HCID 68713012HCID 68713012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.85 g (8.4 mmol) of cis-2-(N′-phenyl-hydrazinocarbonyl)-cyclopropanecarboxylic acid were dissolved in 20 ml of tetrahydrofuran and 0.823 g (2.8 mmol) of triphosgene were added. The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure, and the residue dissolved in acetonitrile/DMF. The product was purified by preparative RP HPLC eluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA). After lyophilization, the product was obtained as a white solid. Yield: 980 mg.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in acetonitrile/DMF
  3. customThe product was purified by preparative RP HPLC
  4. washeluting with a gradient of 0 to 100% acetonitrile in water (+0.01% TFA)
  5. customAfter lyophilization, the product was obtained as a white solid

Sources & evidence

ORD record
ord-f6d384f2346643fdaf9fe81157fa5ed4
Source dataset
uspto-grants-2012_10
Patent number
US08299102B2

Reaction notes

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