Triethylamine → N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

HRID 1719452Notes

Reaction equation

HRID 1719452 reaction equation
N(C(CCCCCCCCCCCCCCCCC)=O)[C@H]([C:4]([NH:6][C@@:7](OCC1C=CC=CC=1)([C:13]([O:15][N:16]1[C:21](=[O:22])[CH2:20][CH2:19][C:17]1=[O:18])=[O:14])[CH2:8]CC(=O)O)=[O:5])C.[CH2:50](N(CC)CC)C.C(OCC)(=O)C.[CH3:63][C:64]([CH3:66])=[O:65].O>CC(C)=O>[NH:6]([C:4]([O:65][C:64]([CH3:50])([CH3:66])[CH3:63])=[O:5])[C@@H:7]([C:13]([O:15][N:16]1[C:21](=[O:22])[CH2:20][CH2:19][C:17]1=[O:18])=[O:14])[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18366337Propan-2-one--water (1/1)HCID 131713575HCID 131713575, compound

Product 1

HCID 11580086N-[(1,1-Dimethylethoxy)carbonyl]-D-alanine 2,5-dioxo-1-pyrrolidinyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of Boc-(D)-mesoDAP-(L)-D-AlaOH-(D)-NHNHBoc (2) (2.76 g) and triethylamine in aceton-water (2:1, 90 ml) was added a solution of O-acetylbenziloyl-γ-D-Glu(α-OBzl)-1-succinimidyl ester (3.4 g:5.8 mM) in acetone at 0° C. with stirring. Stirring was continued overnight, allowing the temperature of the mixture to reach to room temperature. After evapolation of acetone, the residue was added ethyl acetate (60 ml), and the organic layer was washed with dil sodium bicarbonate, saturated sodium chloride, dil hydrochloric acid and water. After drying over magnesium sulfate, the solvent was removed in vacuo and triturated with isopropyl ether to give O-acetylbenziloyl-γ-D-Glu(α-OBzl)-(L)-Boc-(D)-mesoDAP-(L)-D-AlaOH-(D)-NHNHBoc (3) (4.63 g).

Workup

  1. stirringStirring
  2. customto reach to room temperature
  3. washthe organic layer was washed with dil sodium bicarbonate, saturated sodium chloride, dil hydrochloric acid and water
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-156c9c2434af412ca92fa21bc4b75f91
Source dataset
uspto-grants-1985_09
Patent number
US04539155

Reaction notes

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