1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 3-(2-(((benzyloxy)carbonyl)(methyl)amino)acetamido)azetidine-1-carboxylate

HRID 1896891Notes

Reaction equation

HRID 1896891 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:16])[CH2:12][C:13]([O-:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[NH2:28][CH:29]1[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]([CH3:16])[CH2:12][C:13]([NH:28][CH:29]1[CH2:30][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:32]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 69510352-(((Benzyloxy)carbonyl)(methyl)amino)acetate

Product 1

HCID 58562550Tert-butyl 3-(2-(((benzyloxy)carbonyl)(methyl)amino)acetamido)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(((benzyloxy)carbonyl)(methyl)amino)acetate (2.12 g, 9.50 mmol, prepared the previous step) and EDCI (1.99 g, 10.4 mmol) were stirred in anhydrous DCM (10 mL) for 15 minutes and then added to a solution of commercially available tert-butyl 3-aminoazetidine-1-carboxylate (1.64 g, 9.52 mmol) and DMAP (220 mg, 1.80 mmol) in DCM (90 mL). The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated ammonium chloride solution, 1 N NaOH solution, brine and the organic layer dried over Na2SO4. After concentration in vacuo, the residue was purified by flash chromatography (silica gel, 0%-5% MeOH/EtOAc) to give a white solid after drying under high vacuum.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated ammonium chloride solution, 1 N NaOH solution, brine
  4. dry with materialthe organic layer dried over Na2SO4
  5. concentrationAfter concentration in vacuo
  6. customthe residue was purified by flash chromatography (silica gel, 0%-5% MeOH/EtOAc)
  7. customto give a white solid
  8. customafter drying under high vacuum

Sources & evidence

ORD record
ord-0144385b393041e19d5e84bbc8dd97f5
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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