2-Amino-2-phenylacetamide → 3-{[(1S)-2-Amino-2-oxo-1-phenylethyl]amino}propane-1-sulfonic acid

HRID 239773

反応式

HRID 239773 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:11])[C:8]([NH2:10])=[O:9])=[CH:3][CH:2]=1.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1>O1CCCC1.O1CCOCC1>[NH2:10][C:8](=[O:9])[C@@H:7]([NH:11][CH2:13][CH2:12][CH2:18][S:15]([OH:17])(=[O:16])=[O:14])[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

参加物

5

反応物 2

HCID 127912-Amino-2-phenylacetamideHCID 14264Propane sultone

生成物 1

HCID 160360603-{[(1S)-2-Amino-2-oxo-1-phenylethyl]amino}propane-1-sulfonic acid収率 38.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of D-Phenylglycine amide (850 mg, 7.5 mmol) in tetrahydrofuran (10 mL) and 1,4-dioxane (4 mL) was added 1,3-propanesultone (818 mg, 6.8 mmol). The solution stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration and washed with acetone (2×20 mL). The solid was dissolved in 50% water/EtOH mL). Dowex Marathon C ion exchange 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 was suspended in acetone (50 mL), filtered and dried in the vacuum oven (50° C.), affording the title compound (720 mg, 34%). 1H NMR (D2O, 500 MHz) δ ppm 7.38 (m, 5H), 4.92, (s, 1H), 3.00 (m, 1H), 2.90 (m, 1H), 2.78 (m, 2H), 1.97 (m, 2H). 13C (D2O, 125 MHz) δ ppm 170.14, 130.95, 130.24, 129.94, 128.74, 63.40, 47.99, 44.92, 21.27. [α]D=+106° (c=0.0016 in water), ES-MS 273 (M+1).

後処理

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetone (2×20 mL)
  4. dissolutionThe solid was dissolved in 50% water/EtOH mL)
  5. additionDowex Marathon C ion exchange 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 the vacuum oven (50° C.)

出典と根拠

ORDレコード
ord-497ddc527a5543ecacbd5f8fdb4364ff
出典データセット
uspto-grants-2014_02
特許番号
US08642801B2

関連ノート

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