Triphenylphosphine → (2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate

HRID 2406760노트

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HRID 2406760 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:46]([O:50][C:51](=[O:60])[NH:52][C@H:53]([CH:55](O)[CH2:56][CH2:57][CH3:58])[CH3:54])([CH3:49])([CH3:48])[CH3:47]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:55]([CH2:56][CH2:57][CH3:58])[C@@H:53]([NH:52][C:51]([O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:60])[CH3:54])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44199404-NitrobenzoateHCID 87514848tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate

생성물 1

HCID 86683881(2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate수율 59.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-nitrobenzoate (16.3 g), triphenylphosphine (32 g), and diisopropyl azodicarboxylate (40% toluene solution) (64 ml) were added dropwise to a tetrahydrofuran (50 ml) solution containing tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate (17 g) for 30 minutes, followed by stirring at room temperature for 14 hours. The solvent was distilled away from the reaction solution under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5.5:1), and a yellow solid of (2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate (17 g) was thus obtained.

후처리

  1. distillationThe solvent was distilled away from the reaction solution under reduced pressure
  2. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5.5:1)

출처 및 근거

ORD 기록
ord-90ffe9cbe28643a4b6e1c6f5d8c39e64
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809371B2

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