Sulfuric Acid → Lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate

HRID 417914노트

반응식

HRID 417914 반응식
[CH3:1][O:2][C:3]([NH:5][CH:6]([CH:11]1[CH2:14][O:13][CH2:12]1)[C:7]([O:9]C)=[O:8])=[O:4].O.[OH-].[Li+:17].S(=O)(=O)(O)O.[Li+].[OH-]>C1COCC1.O.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O.CC(=O)OCC>[CH3:1][O:2][C:3]([NH:5][CH:6]([CH:11]1[CH2:12][O:13][CH2:14]1)[C:7]([O-:9])=[O:8])=[O:4].[Li+:17]

참가 물질

9

반응물 4

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 66648610Methyl 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate

생성물 1

HCID 59264533Lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate수율 114.6%

시약·촉매·용매 4

HCID 61578Diammonium molybdate촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To methyl 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate (50 mg, 0.246 mmol) in THF (2 mL) and water (0.5 mL) was added lithium hydroxide monohydrate (10.33 mg, 0.246 mmol). The resultant solution was allowed to stir overnight at ambient temperature. TLC (1:1 EA/Hex; Hanessian stain [1 g Ce(NH4)2SO4, 6 g ammonium molybdate, 6 ml sulfuric acid, and 100 ml water]) indicated ˜10% starting material remaining. Added an additional 3 mg LiOH and allowed to stir overnight at which time TLC showed no starting material remaining. Concentrated in vacuo and placed on high vac overnight providing 55 mg lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate as a colorless solid. 1H NMR (500 MHz, MeOD) δ ppm 3.39-3.47 (m, 1H) 3.67 (s, 3H) 4.28 (d, J=7.93 Hz, 1H) 4.64 (t, J=6.26 Hz, 1H) 4.68 (t, J=7.02 Hz, 1H) 4.73 (d, J=7.63 Hz, 2H).

후처리

  1. stirringto stir overnight at which time TLC
  2. concentrationConcentrated in vacuo
  3. waitplaced on high vac overnight

출처 및 근거

ORD 기록
ord-774b34745a3c427191f2c3de72aa57a9
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093243B2

반응 노트

불러오는 중…