Tetrahydrofuran → Z-Gly-OSu

HRID 72098Notes

Reaction equation

HRID 72098 reaction equation
[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=[O:4].C1COCC1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:43]1[C:48](=[O:49])[CH2:47][CH2:46][C:44]1=[O:45])=[N+](C)C)C>CCOC(C)=O>[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([O:5][N:43]1[C:48](=[O:49])[CH2:47][CH2:46][C:44]1=[O:45])=[O:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

Product 1

HCID 76177Z-Gly-OSuYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Z-Gly-OH (1.0 g, 4.78 mmol) was added THF (10 ml), DIEA (0.98 ml, 5.74 mmol), and TSTU (1.7 g, 5.74 mmol) and the resulting mixture was stirred at room temperature for 2 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 1.34 g (92%) of Z-Gly-OSu 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-f8eb6631e7f541dd9486b8d1a88e8574
Source dataset
uspto-grants-2014_09
Patent number
US08828923B2

Reaction notes

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