1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(t-butoxycarbonyl)-L-valine p-nitrobenzyl ester

HRID 891698Notes

Reaction equation

HRID 891698 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]O)=[CH:21][CH:20]=1)([O-:18])=[O:17].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:14][C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 692754-Nitrobenzyl alcoholHCID 83693Boc-L-Valine

Product 1

HCID 13992531N-(t-butoxycarbonyl)-L-valine p-nitrobenzyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(t-butoxycarbonyl)-L-valine (2.50 g, 11.5 mmol) in methylene chloride (125 ml) were added p-nitrobenzyl alcohol (3.52 g, 23.0 mmol), WSC (4.41 g, 23.0 mmol) and 4-dimethylaminopyridine (140 mg, 1.15 mmol) in an ice bath. The mixture was stirred at room temperature under an atmosphere of nitrogen for 4.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1) as the eluant to afford N-(t-butoxycarbonyl)-L-valine p-nitrobenzyl ester (3.07 g, yield 76%) as white crystals.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-472897f9ca5f48a08400f941e3225464
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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