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

HRID 1620112노트

반응식

HRID 1620112 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-93705581dad54b999f56bb2df6dc3551
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772320B2

반응 노트

불러오는 중…