1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69544177, compound

HRID 891703Notes

Reaction equation

HRID 891703 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]([CH3:11])[CH3:10])=[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])[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH:9]([CH3:11])[CH3:10])=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 692754-Nitrobenzyl alcoholHCID 10465935N-Boc-N-isopropylamino-acetic acid

Product 1

HCID 69544177HCID 69544177, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Subsequently, to a solution of (N-t-butoxycarbonyl-N-isopropyl-amino)-acetic acid (2.05 g, 9.44 mmol) and p-nitrobenzyl alcohol (2.89 g, 18.9 mmol) in methylene chloride (100 ml) were added WSC (3.62 g, 18.9 mmol) and 4-dimethylaminopyridine (120 mg, 0.98 mmol) in an ice bath under an atmosphere of nitrogen, and then the mixture was stirred at room temperature overnight. 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 magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (5:2) as the eluant to afford (N-t-butoxycarbonyl-N-isopropyl-amino)acetic acid p-nitrobenzyl ester (1.93 g, yield 58%) as a pale yellow transparent syrup.

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 magnesium 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-1c44c424c8a64609aba6f837de1c5674
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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