Triethylamine → HCID 86682349, compound

HRID 2281673Notes

Reaction equation

HRID 2281673 reaction equation
C(O)(=O)C(O)=O.[C:7]([O:11][C:12]([N:14]1[CH2:20][C:16]2([NH:19][CH2:18][CH2:17]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[CH2:29][N:30]=[C:31]=[O:32].C(N(CC)CC)C>C(#N)C>[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[CH2:29][NH:30][C:31]([N:19]1[C:16]2([CH2:15][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[CH2:20]2)[CH2:17][CH2:18]1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46127082,4-Dichlorobenzyl isocyanate2×HCID 56962145tert-butyl 1,6-diazaspiro[3.3]heptane-6-carboxylate, hemioxalate salt

Product 1

HCID 86682349HCID 86682349, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-(tert-butoxycarbonyl)-1,6-diaza-spiro[3.3]heptane oxalate (350 mg, 719 μmol) in acetonitrile (5 mL) was added 2,4-dichloro-1-(isocyanatomethyl)benzene (291 mg, 1.44 mmol) followed by triethylamine (201 μl, 1.44 mmol) and the mixture was stirred overnight. Further 2,4-dichloro-1-(isocyanatomethyl)benzene (100 mg, 0.49 mmol) was added. After 1 hour at ambient temperature, the reaction was concentrated under reduced pressure. The residue was purified by chromatography (SiO2; heptane:ethyl acetate 1:4) to give the title compound (378 mg, 65%) as a colorless foam. MS (EI) m/e: 400.2 (M+H)+.

Workup

  1. waitAfter 1 hour at ambient temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customThe residue was purified by chromatography (SiO2; heptane:ethyl acetate 1:4)

Sources & evidence

ORD record
ord-4a362eda791e4ec3b028d3a6c62f4342
Source dataset
uspto-grants-2015_09
Patent number
US09139593B2

Reaction notes

Loading…