Hydrazine hydrate (1:1) → tert-butyl N-[1-amino-3-(methylsulfanyl)propan-2-yl]carbamate

HRID 1504834ノート

反応式

HRID 1504834 の反応式
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:14][S:15][CH3:16].O.NN>C(O)C>[NH2:3][CH2:12][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:14][S:15][CH3:16]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 24720892tert-Butyl [2-phthalimido-1-(methylsulfanylmethyl)ethyl]carbamate

生成物 1

HCID 72455593tert-butyl N-[1-amino-3-(methylsulfanyl)propan-2-yl]carbamate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(methylsulfanyl)propan-2-yl]carbamate (from Step 3 of PrepEx 4.11) (10.0 g, 28.6 mmol) in ethanol (150 mL) was added dropwise hydrazine hydrate (15.7 g, 286 mmol) at 0° C. and then the reaction mixture was allowed to warm to ambient temperature. After 30 minutes, the reaction mixture was heated to reflux. After two hours, the reaction mixture was cooled, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give tert-butyl [1-amino-3-(methylsulfanyl)propan-2-yl]carbamate. MS ESI calc'd. for C9H21N2O2S [M+H]+ 221. found 221. 1H NMR (400 MHz, CD3OD) δ 3.66-3.63 (m, 1H), 2.83-2.79 (m, 1H), 2.64-2.50 (m, 3H), 2.12 (s, 3H), 1.45 (s, 9H).

後処理

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter two hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-b40620f37a934282a7b5552bd37843b5
出典データセット
uspto-grants-2015_12
特許番号
US09216173B2

反応ノート

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