1,2-Dichloroethane → tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

HRID 1253503Notes

Reaction equation

HRID 1253503 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.C(Cl)CCl.Cl.[CH3:30][NH:31][O:32][CH3:33]>ClCCl.C(N(CC)CC)C>[CH3:33][O:32][N:31]([CH3:30])[C:12]([CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:11]1)=[O:14]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution containing 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (60.4 g, 0.30 mol), hydroxybenzotriazole (49 g, 0.36 mol), EDC (69.4 g, 0.36 mol), and triethyamine (142 ml) in 620 ml of dichloromethane was added N,O-dimethylhydroxyl-amine hydrochloride (35.4 g, 0.36 mol). The mixture obtained was stirred overnight at room temperature. The solution was partitioned between 500 ml of water and 200 ml of dichloromethane, and the aqueous layer was washed with 200 ml of dichloromethane. The combined organic layers were washed with 250 ml of brine, dried over magnesium sulfate, filtered and concentrated to afford tert-butyl 3-{[methoxy(methyl)amino]carbonyl}azetidine-1-carboxylate, which was used without additional purification.

Workup

  1. customThe mixture obtained
  2. customThe solution was partitioned between 500 ml of water and 200 ml of dichloromethane
  3. washthe aqueous layer was washed with 200 ml of dichloromethane
  4. washThe combined organic layers were washed with 250 ml of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c342c56933d34c5eb7650778a5721bf0
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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