Acetonitrile → HCID 66661795, compound

HRID 2275609Notes

Reaction equation

HRID 2275609 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 it 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 it 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 it for 2 h
  6. customThe solvent was removed in-vacuo

Sources & evidence

ORD record
ord-3ca1cef6e58a4a719b35bcbdd6683128
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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