Benzyl chloroformate → HCID 70161058, compound

HRID 842610Notes

Reaction equation

HRID 842610 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[O:6][CH2:7][CH:8]([OH:19])[CH2:9][NH:10][C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])([O-:3])=[O:2].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>[OH:19][CH:8]([CH2:7][O:6][C:5]1[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:9][N:10]([C@@H:11]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])[C:25](=[O:26])[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 70163384HCID 70163384, compound

Product 1

HCID 70161058HCID 70161058, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

The product from Example 1B (31.3 g, 100 mmol) in THF (300 mL) and 10% Na2CO3 (250 mL) at 0° C. was treated dropwise with benzyl chloroformate (18.0 g, 105 mmol), stirred vigorously for 30 minutes, and extracted with diethyl ether. The organic layer was washed with brine, dried (MgSO4), and concentrated to provide the title compound.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-059a819e98be4f2ba311f06b8dfb81bb
Source dataset
uspto-grants-2002_04
Patent number
US06376488B1

Reaction notes

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