Triethylamine → 2-(2-Furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 448745

Reaction equation

HRID 448745 reaction equation
ClC(OCC(C)C)=O.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([NH:16][C:17]1([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=O.C(N(CC)CC)C>O1CCCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[O:25][C:23](=[O:24])[C:17]2([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 174552541-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acid

Product 1

HCID 247399602-(2-Furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (44 mmol) of isobutyl chloroformate was added dropwise to a solution of 10 g (42 mmol) of 1-[(2-furanylcarbonyl)amino]cyclohexanecarboxylic acid obtained in Reference Example 14 and 6.1 ml (44 mmol) of triethylamine in tetrahydrofuran (80 ml), and the mixture was stirred at room temperature for 1 hour. The precipitated crystal was removed by filtration, and the filtrate was concentrated. The obtained crystal was washed with water to obtain 8.95 g (97%) of the title compound.

Workup

  1. customThe precipitated crystal was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. washThe obtained crystal was washed with water

Sources & evidence

ORD record
ord-56437398055d4e46956b7b3a9c83ae26
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Linked notes

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