Sodium Hydroxide → t-Butyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate

HRID 1411116노트

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HRID 1411116 반응식
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6]N.[OH-:22].[Na+]>O.O1CCOCC1.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[N-]=O.O.O.[Na+].[Na+].[Fe+4]>[C:18]([O:17][C:15]([NH:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][OH:22])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:16])([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 10470194(S)-tert-Butyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate

생성물 1

HCID 10924706t-Butyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate수율 37%

시약·촉매·용매 3

HCID 11953895Sodium nitroprusside dihydrate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
65 °C

실험 절차

A vigorously stirred solution of Boc-Lys-OtBu 2 (6.20 g, 20.5 mmol) in water (120 mL) and dioxane (60 mL) was warmed to 65° C. and treated with sodium nitroprusside (SNP, Na2[Fe(CN)5NO].2H2O) (9.8 g, 33 mmol) portionwise over 1 hour. The reaction mixture was stirred at 65° C. for an additional 4 hours while its pH was maintained at 9-10 by addition of 2M NaOH. It was then cooled to room temperature and filtered through a pad of CELITE. The filtrate was extracted with EtOAc (6×100 mL) and the combined extracts were dried (MgSO4), filtered, and evaporated in vacuo to give a purple oil. Its purification by flash chromatography (silica gel; hexanes/EtOAc, 8/1→3/7) gave the title compound 25 (2.28 g, 37%) as a clear oil.

후처리

  1. temperatureIt was then cooled to room temperature
  2. filtrationfiltered through a pad of CELITE
  3. extractionThe filtrate was extracted with EtOAc (6×100 mL)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a purple oil
  8. customIts purification by flash chromatography (silica gel; hexanes/EtOAc, 8/1→3/7)

출처 및 근거

ORD 기록
ord-fd08125bd571488ea4e0e722cd030035
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921571B2

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