Acetone Cyanohydrin → 1,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoate

HRID 1160403노트

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HRID 1160403 반응식
[NH2:1][CH2:2][C@@H:3]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([Cl:21])[CH:14]=1)[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:22][C:23](C)(O)[C:24]#N>CCO>[Cl:21][C:15]1[CH:14]=[C:13]([NH:12][C@H:3]([CH2:2][NH:1][CH:23]([CH3:24])[CH3:22])[CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])[CH:18]=[CH:17][C:16]=1[C:19]#[N:20]

참가 물질

4

반응물 2

HCID 6406Acetone CyanohydrinHCID 595161531,1-Dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate

생성물 1

HCID 595162251,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(1-methylethyl)amino]butanoate수율 94%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

A mixture of 1,1-dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate (0.309 g, 1 mmol), acetone cyanohydrin (0.1 g, 1.18 mmol) and crushed 4 Å molecular sieves in EtOH (5 mL) was stirred at 60° C. for 6 h. After cooled down, the reaction mixture was filtered. The filtrate was treated with NaBH4 (excess amount) and stirred for 2.5 h. The reaction was diluted with H2O and extracted with Et2O (2×). The organic extracts were washed with H2O (2×), dried over Na2SO4, filtered, and concentrated to yield the titled product (0.33 g, 94%). LC-MS (ES) m/e 352.5 (M+H)+.

후처리

  1. temperatureAfter cooled down
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was treated with NaBH4 (excess amount)
  4. stirringstirred for 2.5 h
  5. additionThe reaction was diluted with H2O
  6. extractionextracted with Et2O (2×)
  7. washThe organic extracts were washed with H2O (2×)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ea74e2e89dea42b4ab495bd56349f31b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816395B2

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