Methyl chloroformate → HCID 67148244, compound

HRID 2428159Notes

Reaction equation

HRID 2428159 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].C([O-])([O-])=O.[K+].[K+].[C:12]([O:16][C:17](=[O:33])[N:18]([CH2:22][C:23]1[CH:28]=[C:27]([CH2:29][CH2:30][NH2:31])[CH:26]=[CH:25][C:24]=1[Cl:32])[CH:19]1[CH2:21][CH2:20]1)([CH3:15])([CH3:14])[CH3:13]>CC(C)=O>[CH3:5][O:4][C:2](=[O:3])[NH:31][CH2:30][CH2:29][C:27]1[CH:26]=[CH:25][C:24]([Cl:32])=[C:23]([CH2:22][N:18]([C:17]([O:16][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:33])[CH:19]2[CH2:20][CH2:21]2)[CH:28]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 67148610HCID 67148610, compound

Product 1

HCID 67148244HCID 67148244, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl chloroformate (1.72 mL, 21.9 mmol) and K2CO3 (7.65 g, 54.8 mmol) were added to a sol. of [5-(2-amino-ethyl)-2-chloro-benzyl]-cyclopropyl-carbamic acid tert-butyl ester (1.78 g, 5.48 mmol) in acetone (8.00 mL). The mixture was refluxed overnight, and was allowed to cool to rt. The mixture was partitioned between water and CH2Cl2, and the aq. layer was extracted with CH2Cl2 (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 6:4) yielded the title compound (1.41 g, 67%). LC-MS: tR=1.03 min; ES+: 383.50.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe mixture was partitioned between water and CH2Cl2
  3. extractionthe aq. layer was extracted with CH2Cl2 (3×)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (heptane/EtOAc 6:4)

Sources & evidence

ORD record
ord-c3a6b4ecb8b24dccb66e9e03a611c890
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…