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

HRID 1620112ノート

反応式

HRID 1620112 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-93705581dad54b999f56bb2df6dc3551
出典データセット
uspto-grants-2014_07
特許番号
US08772320B2

反応ノート

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