Benzylamine → HCID 86751385, compound

HRID 1489166Notes

Reaction equation

HRID 1489166 reaction equation
[CH2:1]([O:3][C:4]([C@:6]1([C:20]([OH:22])=O)[CH2:10][C:9](=[O:11])[N:8]([C@@H:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])[CH3:2].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:48]([NH2:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>O1CCCC1>[CH2:48]([NH:55][C:20]([C@@:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][C:9](=[O:11])[N:8]([C@@H:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:22])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 69172662HCID 69172662, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86751385HCID 86751385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-3-Ethoxycarbonyl-1-((S)-α-methylbenzyl)-5-oxopyrrolidine-3-carboxylic acid (10 g) was dissolved in tetrahydrofuran (100 ml). Hydroxybenztriazole (0.89 g) was added and the mixture was stirred. Dicyclohexylcarbodiimide (6.76 g) and benzylamine (3.86 g) were added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was allowed to stand for 2 days and filtered through Celite. The filtrate was concentrated under reduced pressure. Ethyl acetate was added, and the mixture was washed with an aqueous solution of potassium carbonate, water, dilute hydrochloric acid and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The obtained oil was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to give the object compound as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionEthyl acetate was added
  6. washthe mixture was washed with an aqueous solution of potassium carbonate, water, dilute hydrochloric acid
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  8. customThe obtained oil was purified by silica gel column chromatography (developing solvent, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-bc8632bf32e94a7da79f8617e4ba738a
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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