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

HRID 1896802Notes

Reaction equation

HRID 1896802 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-d8ceb96ae10440858ee7a315a82f463d
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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