Triethylamine → tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)azetidine-1-carboxylate

HRID 1441242Notes

Reaction equation

HRID 1441242 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1.C(N(CC)CC)C.[C:21](C(CC(N)=O)C(N)=O)([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>CN(C=O)C>[C:25]1([CH2:24][O:23][C:21]([NH:1][CH2:2][CH:3]2[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]2)=[O:22])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10679125Tert-butyl 3-(aminomethyl)azetidine-1-carboxylateHCID 18460661HCID 18460661, compound

Product 1

HCID 45072305tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)azetidine-1-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-(aminomethyl)-1-azetidinecarboxylate (5.0 g, 26.84 mmole) in DMF (40 mL) was added triethylamine (4.9 mL, 34.9 mmole) and Cbz-succinamide (8.7 g, 34.9 mmole). After 18 hours, the reaction solution was concentrated under vacuum and redissolved in EtOAc (250 mL). The organic solution was washed with H2O (2×150 mL), brine (100 mL) and dried over Na2SO4 and concentrated. The remaining residue was purified on silica (hexanes/EtOAc, 1:1) to give the title compound (5.5 g, 64%) as a light yellow oil: LC-MS (ES) m/e 321 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. dissolutionredissolved in EtOAc (250 mL)
  3. washThe organic solution was washed with H2O (2×150 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe remaining residue was purified on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-54ab8be5234d47f298974c46568dc856
Source dataset
uspto-grants-2010_02
Patent number
US07655648B2

Reaction notes

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