Water → HCID 86680394, compound

HRID 83585Notes

Reaction equation

HRID 83585 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:12][CH:11]([C:13]([OH:15])=O)[C:8]2([CH2:10][CH2:9]2)[C:7]1=[O:16].[CH2:23]([C@@H:30]1[CH2:34][O:33][C:32](=[O:35])[NH:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN=C=NCCCN(C)C.Cl.O>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:23]([C@@H:30]1[CH2:34][O:33][C:32](=[O:35])[N:31]1[C:13]([CH:11]1[C:8]2([CH2:9][CH2:10]2)[C:7](=[O:16])[N:6]([CH2:5][C:4]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:3]=2[O:2][CH3:1])[CH2:12]1)=[O:15])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 866803935-(2,4-Dimethoxybenzyl)-4-oxo-5-azaspiro[2.4]heptane-7-carboxylic Acid

Product 1

HCID 86680394HCID 86680394, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5-(2,4-dimethoxybenzyl)-4-oxo-5-azaspiro[2.4]heptane-7-carboxylic acid (1.59 g) in chloroform (16 ml) were sequentially added (R)-4-benzyl-2-oxazolidinone (1.11 g), WSC.HCl (1.20 g) and N,N-dimethyl-4-aminopyridine (318 mg) at room temperature, and the mixture was stirred for 4 hours. To this reaction mixture was added water, and the organic layer was separated from the solution, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to separate a low-polarity component as the titled compound (1.39 g).

Workup

  1. customat room temperature
  2. customthe organic layer was separated from the solution
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)
  5. customto separate a low-polarity component as the titled compound (1.39 g)

Sources & evidence

ORD record
ord-f9a91d34ee9e4421b589697e0c2533fa
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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