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Triphenylphosphine → [2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester

HRID 496412
ノート
印刷プレビュー

反応式

HRID 496412 の反応式
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[CH:11][C:10]=1[OH:20])([CH3:4])([CH3:3])[CH3:2].[N:22]1([CH2:27][C@@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)O)[CH:26]=[CH:25][N:24]=[CH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CO.C(Cl)Cl.C1COCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=[O:19])[C:13]=2[CH:12]=[CH:11][C:10]=1[O:20][C@@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 707108(R)-2-Imidazol-1-yl-1-phenyl-ethanolHCID 5462977Diethyl azodicarboxylateHCID 20828939(2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-carbamic acid tert-butyl ester

生成物 1

HCID 60029890[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamic acid tert-butyl ester
収率 77%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

A round bottom flask was charged with (2-Hydroxy-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl)-carbamic acid tert-butyl ester (700 mg, 2.40 mmol), (R)-2-imidazol-1-yl-1-phenyl-ethanol (544 mg, 2.89 mmol), triphenylphospine (759 mg, 2.89 mmol) and dry THF (14 mL). After approximately 15 nm, diethylazodicarboxylate (0.46 mL, 2.89 mmol) was added slowly. The reaction was stirred overnight and concentrated to give a yellow oil. Purification by chromatography (10-20% acetone/CH2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a white foam (0.850 g, 1.84 mmol, 77%). The structure was confirmed by NMR and mass spectrometry. MS m/z 462 (M++H).

後処理

  1. concentrationconcentrated
  2. customto give a yellow oil
  3. customPurification by chromatography (10-20% acetone/CH2Cl2

出典と根拠

ORDレコード
ord-8d2587de47044b4fb0169ff59e3e1e00
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06943183B2

反応ノート

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