Acetonitrile → HCID 66661795, compound

HRID 557893Notes

Reaction equation

HRID 557893 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH2:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19]([O:21]C(C)(C)C)=[O:20])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[CH:7]=[CH2:8].C(N(CC)CC)C.C(#N)C>>[CH2:6]([N:9]([C:2]([O:4][CH3:5])=[O:3])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19]([OH:21])=[O:20])[CH2:17][CH2:18]2)=[CH:12][CH:11]=1)[CH:7]=[CH2:8]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 66662345HCID 66662345, compound

Product 1

HCID 66661795HCID 66661795, compound

Procedure

Methyl chloroformate (34 μL, 0.00044 mol) was added to a mixture of tert-butyl 1-[4-(allylamino)phenyl]cyclopropanecarboxylate (6.0×10−1 mg, 0.00022 mol) and triethylamine (92 μL, 0.00066 mol) in acetonitrile (1.0 mL, 0.019 mol) at rt. The reaction mixture was stirred at rt for 30 minutes, then was washed with water, and then extracted with EtOAc (3×). The organic layers were combined and concentrated. To the residue was added 4.0M HCl in dioxane and the reaction was stirred at rt for 2 h. The solvent was removed in-vacuo and used in the following step. LC/MS: 276.2 (M+H+).

Workup

  1. washwas washed with water
  2. extractionextracted with EtOAc (3×)
  3. concentrationconcentrated
  4. additionTo the residue was added 4.0M HCl in dioxane
  5. stirringthe reaction was stirred at rt for 2 h
  6. customThe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-50f2aaa9983c40b8b04f8ba6e200348e
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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