p-Toluenesulfonic acid monohydrate → benzyl 3-[(E)-C-(3,3-dimethoxypropyl)-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]azetidine-1-carboxylate

HRID 1972942Notes

Reaction equation

HRID 1972942 reaction equation
[CH3:1][O:2][CH:3]([O:22][CH3:23])[CH2:4][CH2:5][C:6]([CH:8]1[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:9]1)=O.C([O:28][C:29](=[O:32])[NH:30][NH2:31])CCC.O.[C:34]1([CH3:44])[CH:39]=CC(S(O)(=O)=O)=C[CH:35]=1>C(Cl)Cl>[C:34]([O:32][C:29]([NH:30]/[N:31]=[C:6](/[CH:8]1[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:9]1)\[CH2:5][CH2:4][CH:3]([O:22][CH3:23])[O:2][CH3:1])=[O:28])([CH3:44])([CH3:39])[CH3:35]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12936820ButylcarbazateHCID 58529803Benzyl 3-(4,4-dimethoxybutanoyl)azetidine-1-carboxylate

Product 1

HCID 58529451benzyl 3-[(E)-C-(3,3-dimethoxypropyl)-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl 3-(4,4-dimethoxybutanoyl)azetidine-1-carboxylate (1.91 g, 5.94 mmol) in CH2Cl2 (30 mL) was treated with Pert-butylcarbazate (824 mg, 6.24 mmol) followed by para-toluensulfonic acid monohydrate (170 mg, 0.89 mmol). The reaction was stirred at rt for 16 h. The mixture was washed with H2O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine. The organic phase was dried (Na2SO4), filtered and concentrated to afford 2.47 (95%) of the desired product. ES-MS m/z 458.47 [M+Na]+, HPLC RT (min) 3.32.

Workup

  1. washThe mixture was washed with H2O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c4459051f1a441aab8f38b79261c772
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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