Ethyl Acetate → HCID 131727749, compound

HRID 1434507Notes

Reaction equation

HRID 1434507 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:2][C:3]([O:5]N1C(=O)CCC1=O)=O.CCN(C(C)C)C(C)C.[NH2:32][C@H:33]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[OH:37].CCOC(C)=O>CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:2][C:3]([NH:32][C@H:33]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34][CH2:35][C:36](=[O:37])[OH:38])=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 76177Z-Gly-OSuHCID 81531DiisopropylethylamineHCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamate

Product 1

HCID 131727749HCID 131727749, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Z-Gly-OSu (1.3 g, 4.25 mmol) was dissolved in DMF (15 ml) and DIEA (1.82 ml, 10.6 mmol) and H-Glu-OtBu (0.949 g, 4.67 mmol) were added and the resulting mixture was stirred at room temperature for 16 hours. AcOEt (100 ml) was added and the mixture was washed with 0.2N hydrochloric acid (100 ml) and water (2×100 ml). The organic phase was dried (Na2SO4) and concentrated in vacuo to afford 1.7 g (quant.) of Z-Gly-Glu-OtBu as an oil.

Workup

  1. washthe mixture was washed with 0.2N hydrochloric acid (100 ml) and water (2×100 ml)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd1e260722114ee580a6392c99d648af
Source dataset
uspto-grants-2009_11
Patent number
US07615532B2

Reaction notes

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