Butylamine → HCID 9874043, compound

HRID 2297728Notes

Reaction equation

HRID 2297728 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[C:6]1(C2C=CC=CC=2)[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:23][C:24]([N:26]([CH:32]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:33][S:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[C:14](OC2C=CC=CC=2)=[O:15])=[CH:8][CH:7]=1>O1CCCC1>[C:6]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:23][C:24]([N:26]([CH:32]([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:33][S:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])=[O:25])[C:14]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:15])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 8007ButylamineHCID 86586961HCID 86586961, compound

Product 1

HCID 9874043HCID 9874043, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butylamine (0.35 ml) is added to a solution of phenyl (2S)-3-(4-biphenylyl)-2-[3-[(1RS)-1-(ethoxycarbonylmethyl)-2-(phenylthio)ethyl]-3-isoamylureido]propionate (Compound No. 1-80, 464 mg) in tetrahydrofuran (7 ml), and the mixture is stirred at room temperature for 1.5 hours. The reaction mixture is concentrated under reduced pressure, water is added to the concentrate, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 402 mg (90%) of the titled compound (Compound No. 38-1).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, water
  2. additionis added to the concentrate
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe organic layer is washed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca1f5da323f44b71bfa4177e74342042
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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