Hydrazine → tert-butyl N-(2-aminoethyl)-3-methyl-L-valinate

HRID 1174297ノート

反応式

HRID 1174297 の反応式
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][NH:14][C@H:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([CH3:19])([CH3:18])[CH3:17].NN>C(O)C>[NH2:3][CH2:12][CH2:13][NH:14][C@H:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([CH3:18])([CH3:19])[CH3:17]

参加物

4

反応物 2

HCID 9321HydrazineHCID 67407870tert-butyl(2S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3,3-dimethylbutanoate

生成物 1

HCID 86599577tert-butyl N-(2-aminoethyl)-3-methyl-L-valinate収率 93.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
75 °C

実験手順

The product of Example 111-2 (87 g, 241.6 mmol) was taken up in ethanol (2 L) in a 3-necked, 3L round bottom flask equipped with mechanical stirring under N2. Hydrazine (anhydrous, 68.3 mL, 2.17 mol, 9 equivalents) was added. The reaction mixture was heated to 75° C., which resulted in the formation of a very thick suspension. The addition of more ethanol was necessary in order to continue effective stirring. The reaction was stirred for 1 hour at 75° C. until consumption of starting material was complete as determined by HPLC. The thick suspension was cooled to ambient temperature and quenched with 1 L of 0.5N NaOH solution. The mixture was diluted with 0.5N NaOH (2 L) and extracted with dichloromethane (2×2 L). The combined organic layer was washed with brine (1 L), dried over MgSO4, filtered and concentrated to oil. The oil was chased with heptanes to remove ethanol and pump dried to afford light yellow oil (50.2 g, 93.2% yield). 1H NMR (CDCl3): δ 2.73(m, 4H), 2.45(m, 1H), 1.64(s, 9H), 0.96(s, 9H).

後処理

  1. customequipped
  2. customwhich resulted in the formation of a very thick suspension
  3. stirringThe reaction was stirred for 1 hour at 75° C. until consumption of starting material
  4. temperatureThe thick suspension was cooled to ambient temperature
  5. customquenched with 1 L of 0.5N NaOH solution
  6. additionThe mixture was diluted with 0.5N NaOH (2 L)
  7. extractionextracted with dichloromethane (2×2 L)
  8. washThe combined organic layer was washed with brine (1 L)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to oil
  12. customto remove ethanol and pump
  13. customdried

出典と根拠

ORDレコード
ord-f6fbb4d3ee6148068649d2b86f1a743b
出典データセット
uspto-grants-2010_11
特許番号
US07834043B2

反応ノート

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