Z-Gly-Gly-OtBu → Tert-butyl 2-(2-aminoacetamido)acetate

HRID 452333Notes

Reaction equation

HRID 452333 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4]>C1COCC1.[Pd]>[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4]

Participants

4

Reactant 1

HCID 15403804Z-Gly-Gly-OtBu

Product 1

HCID 15403805Tert-butyl 2-(2-aminoacetamido)acetateYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

36.5 g (113 mmol) of Z-Gly-Gly-OtBu were dissolved in 11 THF followed by the addition of 3.65 g palladium on charcoal (10%). The mixture was stirred under H2 atmosphere (1 atm) for 3 h at room temperature. The suspension was purged with N2, filtered (PTFE-filter: 0.45 μm) and the filtrate was concentrated under reduced pressure yielding 20.3 g (95%) Gly-Gly-O-tBu as a yellow oil. The crude material was pure enough for further synthesis.

Workup

  1. customThe suspension was purged with N2
  2. filtrationfiltered
  3. filtration(PTFE-filter: 0.45 μm)
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dff45dc001e74724995aedf1fe4a1b03
Source dataset
uspto-grants-2013_07
Patent number
US08491906B2

Reaction notes

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