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

HRID 1972942노트

반응식

HRID 1972942 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c4459051f1a441aab8f38b79261c772
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431695B2

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