HCID 86752719, compound → HCID 86752718, compound

HRID 963180Notes

Reaction equation

HRID 963180 reaction equation
C([NH:8][C@H:9]([C:22]([NH:24][CH2:25][CH2:26][NH:27][C:28]([CH:30]=[CH:31][CH3:32])=[O:29])=[O:23])[CH:10]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11](=[O:13])[OH:12])(OC(C)(C)C)=O>O1CCOCC1>[CH2:15]([O:14][CH:10]([C:11](=[O:12])[OH:13])[C@@H:9]([C:22]([NH:24][CH2:25][CH2:26][NH:27][C:28]([CH:30]=[CH:31][CH3:32])=[O:29])=[O:23])[NH2:8])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 86752719HCID 86752719, compound

Product 1

HCID 86752718HCID 86752718, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Boc-Asp(OBzl) (12.9 g) was dissolved in tetrahydrofuran (100 ml) and added with N-methylmorpholine (4.0 g) and isobutyl chloroformate (5.44 g) with cooling at -10° C. After stirring for 15 minutes, the mixture was added with ethylenediamine monomethacrylic acid hydrochloride (4.0 g) and N-methylmorpholine (3.0 g) and stirred. One hour later, the solvent was evaporated under reduced pressure and the residue was dissolved in chloroform. The organic layer was washed with saturated aqueous solution of sodium hydrogen carbonate and 10% aqueous solution of citric acid and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was subjected to silica gel chromatography to collect fractions of dichloromethane/ethyl acetate=25/75 to give N-Boc-β-benzyloxy-L-aspartylaminoethylaminocarbonyl-2-methylethene (3.3 g). N-Boc-β-benzyloxy-L-aspartylaminoethylaminocarbonyl-2-methylethene (3.3 g) was dissolved in dioxane (50 ml) and the Boc group was removed by adding 4M-hydrochloric acid solution in dioxane (50 ml) to give β-benzyloxy-L-aspartylaminoethylaminocarbonyl-2-methylethene (2.9 g).

Workup

  1. customthe Boc group was removed
  2. additionby adding 4M-hydrochloric acid solution in dioxane (50 ml)

Sources & evidence

ORD record
ord-1183bdbca74546b484a843ed0728e45c
Source dataset
uspto-grants-1998_06
Patent number
US05763408

Reaction notes

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