Ethyl Acetate → HCID 131727749, compound

HRID 72099Notes

Reaction equation

HRID 72099 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-069b300fbc8b498f8f33a663d9849eba
Source dataset
uspto-grants-2014_09
Patent number
US08828923B2

Reaction notes

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