Benzyl chloroformate → HCID 19705542, compound

HRID 589200Notes

Reaction equation

HRID 589200 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C:4](=[O:7])[NH:3]1.CCN(C(C)C)C(C)C.[C:17](Cl)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C(Cl)Cl>[O:7]=[C:4]1[CH2:5][CH2:6][N:2]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[NH:3]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 27337123-Pyrazolidinone hydrochloride

Product 1

HCID 19705542HCID 19705542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of pyrazolidin-3-one hydrogen chloride (5.00 g, 40.8 mmol) in DCM (120 mL) at 0° C. was added DIEA (2.5 eq), followed by CbzCl (1.15 eq). The resulting clear solution was warmed to it and stirred 3 h. The reaction mixture was washed with brine. The aqueous layer was separated and back-extracted with DCM (×2). The combined organic layers were dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-100% EtOAc/Hexanes, Rf=0.35 in 100% EtOAc) to afford the desired product as a white solid (5.31 g).

Workup

  1. temperatureThe resulting clear solution was warmed to it
  2. washThe reaction mixture was washed with brine
  3. customThe aqueous layer was separated
  4. extractionback-extracted with DCM (×2)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by a SiO2 column (0-100% EtOAc/Hexanes, Rf=0.35 in 100% EtOAc)

Sources & evidence

ORD record
ord-327503e20daf4709984027d54ea6de4e
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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