2,2,2-Trifluoroethanol → (2R,3S)-3-acetamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide

HRID 61349

反応式

HRID 61349 の反応式
[CH2:1]([CH:4]1[C:8](=O)[CH2:7][CH2:6][O:5]1)[CH:2]=[CH2:3].[C:10]([O-:13])(=O)[CH3:11].[NH4+:14].[C:15]([N+:19]#[C-])([CH3:18])([CH3:17])[CH3:16].FC(F)(F)[CH2:23][OH:24]>O>[C:10]([NH:14][C@@:8]1([C:23]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:24])[CH2:7][CH2:6][O:5][C@@H:4]1[CH2:1][CH:2]=[CH2:3])(=[O:13])[CH3:11]

参加物

6

反応物 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 136645612-(Prop-2-en-1-yl)oxolan-3-one

生成物 1

HCID 67513020(2R,3S)-3-acetamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide収率 36%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2-allyldihydrofuran-3(2H)-one (1.2 g, 9.5 mmol) and ammonium acetate (4.39 g, 57.0 mmol) in 2,2,2-trifluoroethanol (5 mL) was treated with tert-butyl isocyanide (2.37 g, 3.23 mL, 28.5 mmol). After stirring at room temperature for 5 days, the reaction mixture diluted with water (50 mL) and extracted using ethyl acetate (2×50 mL). The combined organic layers were washed with saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated. Purification by flash column chromatography (silica gel, 50% ethyl acetate in methylene chloride) gave (2R 3S)-3-acetamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide as a colorless oil (930 mg, 36%) and (2S,3S)-3-acetylamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide as a colorless oil (650 mg, 26%). Analytical data for (2R,3S)-3-acetylamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide: 1H NMR (CDCl3, 300 MHz) δ 6.65 (s, NH, 1 H), 6.06 (s, NH, 1 H), 5.86 (m, 1 H), 5.16 (m, 2 H), 4.20 (dd, J1=9 Hz, J2=4 Hz, 1 H), 3.82 (m, 2 H), 2.54 (m, 2 H), 2.20-2.40 (m, 2 H), 2.03 (s, 3 H), 1.32 (s, 9 H); MS (+CI): m/z for C14H24N2O3: expected 268.2; found 269.2 (M+H)+.

後処理

  1. extractionextracted
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (silica gel, 50% ethyl acetate in methylene chloride)

出典と根拠

ORDレコード
ord-6c33de829c4f4d8b958956cab7162fa8
出典データセット
uspto-grants-2016_09
特許番号
US09440995B2

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