Benzyl chloroformate → HCID 178523560, compound

HRID 892340Notes

Reaction equation

HRID 892340 reaction equation
[NH2:1][CH:2]([C:6]1[CH:18]=[CH:17][C:9]2[NH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[N:12][C:8]=2[CH:7]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[CH2:25]([O:24][C:22]([NH:1][CH:2]([C:6]1[CH:18]=[CH:17][C:9]2[NH:10][C:11]([C:13]([F:15])([F:16])[F:14])=[N:12][C:8]=2[CH:7]=1)[C:3]([OH:5])=[O:4])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 178511451HCID 178511451, compound

Product 1

HCID 178523560HCID 178523560, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.2 g (27.1 mmol) of 14f are dissolved in 50 ml of water, and the pH is adjusted to 9 with 2N sodium hydroxide solution. The clear solution is cooled to 0°-5° C., and 8.1 ml (0.0569 mol) of benzyl chloroformate are added dropwise within 30 minutes, with simultaneous addition of 2N sodium hydroxide solution (pH range 8-10). After stirring at room temperature for 50 minutes, the mixture is extracted once with ether/ethyl acetate (1:1), and the aqueous phase is acidified to pH 2 with 2N HCl and is extracted with ethyl acetate. After washing with water and drying over Na2SO4, the residue is reprecipitated from ethyl acetate/petroleum ether.

Workup

  1. temperatureThe clear solution is cooled to 0°-5° C.
  2. extractionthe mixture is extracted once with ether/ethyl acetate (1:1)
  3. extractionis extracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialdrying over Na2SO4
  6. customthe residue is reprecipitated from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e7bcad9c5433441a9eb7f9c708bd9748
Source dataset
uspto-grants-1992_06
Patent number
USRE033948

Reaction notes

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