Benzyl chloroformate → HCID 123932151, compound

HRID 1778528Notes

Reaction equation

HRID 1778528 reaction equation
[Si:1]([O:8][CH:9]1[CH2:15][CH:14]2[NH:16][CH:10]1[CH2:11][C:12](=[CH:17][C:18]([O:20][CH3:21])=[O:19])[CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:22](Cl)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C(Cl)Cl>[Si:1]([O:8][CH:9]1[CH2:15][CH:14]2[N:16]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH:10]1[CH2:11][CH:12]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 131734824HCID 131734824, compound

Product 1

HCID 123932151HCID 123932151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 109d (40 g, 0.13 mol, 1.0 eq) and TEA (40 g, 0.39 mol, 3.0 eq) in DCM (800 mL) was added a solution of CbzCl (45 g, 0.26 mol, 2.0 eq) in DCM (150 mL) slowly. The resulting mixture was stirred at room temperature for 16 h. The mixture was quenched with water, washed with 1N HCl (500 mL), the organic layer was dried over Na2SO4 and concentrated to give benzyl 6-[tert-butyl(dimethyl)silyl]oxy-3-(2-methoxy-2-oxo-ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate 109e as a crude product.

Workup

  1. customThe mixture was quenched with water
  2. washwashed with 1N HCl (500 mL)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-20f86282ae4e4a149e46d5df4df718b0
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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