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

HRID 2175486Notes

Reaction equation

HRID 2175486 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[NH2:27][CH:28]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29]1.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:27][CH:28]1[CH2:29][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:31]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14349BenzyloxycarbonylglycineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of commercially available 2-(((benzyloxy)carbonyl)amino)acetic acid (6.70 g, 32.0 mmol) and EDCI (8.42 g, 43.9 mmol) was stirred in anhydrous DCM for 15 minutes and then added to a solution of commercially available tert-butyl 3-aminoazetidine-1-carboxylate (5.02 g, 29.1 mmol) and HOBt (4.45 g, 29.0 mmol, mono hydrate). 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-922132f15ad84688adab59d5c2cfb67f
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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