Propane sultone → 3-{[(1R)-1-(aminocarbonyl)-2-methylpropyl]amino}1-propanesulfonic acid

HRID 239779

반응식

HRID 239779 반응식
[NH2:1][C@@H:2]([C:6]([NH2:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH2:9]1[CH2:15][S:12](=[O:14])(=[O:13])[O:11][CH2:10]1>C(#N)C>[NH2:8][C:6]([C@H:2]([NH:1][CH2:10][CH2:9][CH2:15][S:12]([OH:14])(=[O:13])=[O:11])[CH:3]([CH3:5])[CH3:4])=[O:7]

참가 물질

4

반응물 2

HCID 14264Propane sultoneHCID 444079(R)-2-amino-3-methylbutanamide

생성물 1

HCID 160361793-{[(1R)-1-(aminocarbonyl)-2-methylpropyl]amino}1-propanesulfonic acid수율 51%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of D-valinamide (1.76 g, 14.7 mmol) in acetonitrile (30 mL) was slowly added 1,3-propanesultone (1.75 g, 14.4 mmol). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetonitrile (2×25 mL). The solid product was dissolved in water (75 mL). Dowex Marathon C resin (strongly acidic) was added to the solution. The suspension was stirred for 15 minutes before the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The solid material was suspended in acetone (50 mL), filtered and dried in vacuo, affording the title compound (1.57 g, 51%). 1H NMR (D2O, 500 MHz) δ ppm 3.80 (m, 1H), 3.19 (m, 2H), 3.00 (m, 2H), 2.25 (m, 1H), 2.16 (m, 2H), 1.08 (d, 3H, J=6.8 Hz), 1.02 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) δ ppm 169.94, 65.86, 48.10, 46.27, 29.54, 21.23, 17.99, 17.02. [α]D=−12.4° (c=0.0037 in water), ES-MS 237 (M−1).

후처리

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetonitrile (2×25 mL)
  4. dissolutionThe solid product was dissolved in water (75 mL)
  5. additionDowex Marathon C resin (strongly acidic) was added to the solution
  6. stirringThe suspension was stirred for 15 minutes before the resin
  7. customwas removed by filtration
  8. customThe filtrate was evaporated under reduced pressure
  9. filtrationfiltered
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-c3eb7f52c8e7413f8ebba8dd6edd4db6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642801B2

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