Benzyl chloroformate → HCID 11161871, compound

HRID 1661529Notes

Reaction equation

HRID 1661529 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[NH2:21][C:22]1[CH:31]=[CH:30][C:25]2[C:26](=[O:29])[CH2:27][O:28][C:24]=2[CH:23]=1>C1COCC1>[CH2:14]([O:13][C:11](=[O:12])[NH:21][C:22]1[CH:31]=[CH:30][C:25]2[C:26](=[O:29])[CH2:27][O:28][C:24]=2[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformate2×HCID 81531DiisopropylethylamineHCID 55264285HCID 55264285, compound

Product 1

HCID 11161871HCID 11161871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

54.7 ml (314 mmol) of diisopropylethylamine and 28.3 ml (188 mmol) of benzyl chloroformate are added to a solution of 23.42 g (157 mmol) of 6-amino-1-benzofuran-3(2H)-one in 400 ml of THF at 0° C. and the mixture is stirred at room temperature for 3 hours. Then a further 4.7 ml (31 mmol) of benzyl chloroformate are added, and the mixture is stirred overnight. The mixture is added to ice-water and extracted twice with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Chromatography on silica gel 60 (mobile phase: dichloromethane→dichloromethane/ethyl acetate 5:1) affords 30.80 g (64% of theory) of the product as colorless crystals.

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic phases are washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e86ca0c6d704763a4e05f6978879507
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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