1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester

HRID 580830Notes

Reaction equation

HRID 580830 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:36]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:37]([C:40](O)=[O:41])[CH2:38][OH:39].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[CH2:12]([O:19][C:20](=[O:35])[C@H:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:22][C:38](=[O:39])[C@H:37]([CH2:40][OH:41])[NH:36][C:43]([O:45][C:46]([CH3:47])([CH3:49])[CH3:48])=[O:44])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 13233366L-Glutamic acid dibenzyl ester tosylate

Product 1

HCID 67584326N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl esterYield 94.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of L-glutamic acid 1,5-dibenzyl ester p-toluenesulfonate (10.0 g), Boc-Ser (4.1 g) and TEA (2.0 g) in DMF (200 ml) are added with stirring WSC (5.0 g) and HOBt (4.0 g) under ice-cooling. The mixture is stirred at room temperature for 20 hours, and thereto is added ethyl acetate (200 ml). The mixture is washed successively with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The precipitated solid is collected by filtration, and washed with ether to give N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1,5-dibenzyl ester (9.7 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. washThe mixture is washed successively with 1N hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitated solid is collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-a409ba1f32764a15a36baead25c90546
Source dataset
uspto-grants-1999_07
Patent number
US05919769

Reaction notes

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