Ethyl Acetate → N-[[1-[[(1H-Pyrrol-2-yl)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol

HRID 1851863Notes

Reaction equation

HRID 1851863 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1C(=O)[C:9](=[O:12])[C:8]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[N:7]=1.[NH2:18][C@H:19]([CH2:23][OH:24])[CH:20]([CH3:22])[CH3:21].C(OCC)(=[O:27])C>>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:7][C:8]1([C:9]([NH:18][C@H:19]([CH2:23][OH:24])[CH:20]([CH3:22])[CH3:21])=[O:12])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:27]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 640993L-ValinolHCID 671808492-(1H-pyrrol-2-yl)-3-oxo-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 57672919N-[[1-[[(1H-Pyrrol-2-yl)carbonyl]amino]cyclohexyl]carbonyl]-L-valinolYield 76.4%

Procedure

220 mg (1.01 mmol) of 2-(1H-pyrrol-2-yl)-3-oxo-1-azaspiro[4.5]dec-1-en-4-one was added to a solution of 252 mg (2.45 mmol) of L-valinol in 5 ml of ethyl acetate, and the mixture was stirred at room temperature for 4 days. The reaction solution was distilled off under reduced pressure and purified by silica gel chromatography to obtain 247 mg (76.4%) of the title compound.

Workup

  1. distillationThe reaction solution was distilled off under reduced pressure
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-193a1f50af0549d997301021057e8223
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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