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Benzoyl isothiocyanate → N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

HRID 930286
ノート
印刷プレビュー

反応式

HRID 930286 の反応式
Cl.[NH2:2][C@@:3]([C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[F:19])([CH3:11])[CH2:4][C@H:5]([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(C(C)C)CC)(C)C.[C:29]([N:37]=[C:38]=S)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN=C=NCCC[N+](C)(C)C.[I-]>C1COCC1.CCOC(C)=O.CCCCCC>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([C@:3]2([CH3:11])[CH2:4][C@@H:5]([C:6]([F:7])([F:8])[F:9])[O:10][C:38]([NH:37][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:2]2)[CH:17]=1
参加物反応条件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 68284Benzoyl isothiocyanateHCID 81531DiisopropylethylamineHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 86732117(2S,4S)-4-amino-4-(5-bromo-2-fluorophenyl)-1,1,1-trifluoropentan-2-ol hydrochloride

生成物 1

HCID 86732116N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide
収率 90.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
50 °C

実験手順

A solution of (2S,4S)-4-amino-4-(5-bromo-2-fluorophenyl)-1,1,1-trifluoropentan-2-ol hydrochloride (4f, 693 mg, 1.890 mmol) in THF (10 mL) was treated with diisopropylethylamine (Aldrich; 823 μL, 4.73 mmol) and stirred for 5 min. Benzoyl isothiocyanate (Aldrich; 280 μL, 2.083 mmol) was added dropwise and the reaction mixture was stirred for 3 h. The reaction mixture was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (Aldrich; 674 mg, 2.270 mmol) and heated to 70° C. for 2 h and subsequently to 50° C. for 16 h. The reaction mixture was concentrated and extracted into EtOAc from saturated brine. The combined organic extracts were dried over MgSO4, concentrated, and purified by flash chromatography on silica gel (Gradient: 0%→25% EtOAc/hexane to give N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (789 mg, 1.718 mmol) as a white solid. MS m/z=460.9 [M+H]+. Calculated for C19H15BrF4N2O2: 459.2

後処理

  1. stirringthe reaction mixture was stirred for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted into EtOAc from saturated brine
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (Gradient

出典と根拠

ORDレコード
ord-0d4b42e25a614545997b2232249e71f8
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296734B2

反応ノート

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