Tert-butyl 3-(2-(((benzyloxy)carbonyl)amino)acetamido)azetidine-1-carboxylate → Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate

HRID 2175487Notes

Reaction equation

HRID 2175487 reaction equation
C(OC([NH:11][CH2:12][C:13]([NH:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)=[O:14])=O)C1C=CC=CC=1>[Pd]>[NH2:11][CH2:12][C:13]([NH:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)=[O:14]

Participants

3

Reactant 1

HCID 58562542Tert-butyl 3-(2-(((benzyloxy)carbonyl)amino)acetamido)azetidine-1-carboxylate

Product 1

HCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a flask containing tert-butyl 3-(2-(((benzyloxy)carbonyl)amino)acetamido)azetidine-1-carboxylate (9.26 g, 25.5 mmol) and a stirbar, was added 10% Pd/C (1.356 g, 1.27 mmol). The flask was evacuated and back filled with argon. Methanol (100 mL) was carefully added via syringe and the flask was evacuated with stirring. It was then back filled with hydrogen and stirred 2 days under a hydrogen balloon. After evacuation with stirring and back filling with argon, the catalyst was removed by filtration over Celite 521 and concentrated in vacuo to afford the product.

Workup

  1. customThe flask was evacuated
  2. additionback filled with argon
  3. additionMethanol (100 mL) was carefully added via syringe
  4. customthe flask was evacuated
  5. additionIt was then back filled with hydrogen
  6. stirringstirred 2 days under a hydrogen balloon
  7. stirringAfter evacuation with stirring
  8. customthe catalyst was removed by filtration over Celite 521
  9. concentrationconcentrated in vacuo
  10. customto afford the product

Sources & evidence

ORD record
ord-daa5c27f36864999a051546d18ae9639
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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