Water → (2R,3S)-3-acetamido-N-tert-butyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)tetrahydrofuran-3-carboxamide

HRID 590694

反応式

HRID 590694 の反応式
[C:1]([NH:4][C@@:5]1([C:13]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8][O:7][C@@H:6]1[CH2:10][CH:11]=[CH2:12])(=[O:3])[CH3:2].[CH3:20][C:21]1([CH3:28])[C:25]([CH3:27])([CH3:26])[O:24][BH:23][O:22]1.O>ClCCl.[Ir+].ClC1CCC=CCCC=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([NH:4][C@@:5]1([C:13]([NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8][O:7][C@@H:6]1[CH2:10][CH2:11][CH2:12][B:23]1[O:24][C:25]([CH3:27])([CH3:26])[C:21]([CH3:28])([CH3:20])[O:22]1)(=[O:3])[CH3:2]

参加物

7

反応物 3

HCID 962WaterHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 67513020(2R,3S)-3-acetamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide

生成物 1

HCID 67516397(2R,3S)-3-acetamido-N-tert-butyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)tetrahydrofuran-3-carboxamide収率 63%

試薬・触媒・溶媒 3

HCID 742671,2-Bis(diphenylphosphino)ethane触媒HCID 178478077HCID 178478077、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of (2R,3S)-3-acetamido-2-allyl-N-tert-butyltetrahydrofuran-3-carboxamide (930 mg, 3.47 mmol) in dichloromethane (20 mL), was treated with chloro-1,5-cyclooctadiene iridium(I) dimer (70 mg, 3 mol %) and 1,2-bis(diphenylphosphino)-ethane (83 mg, 6 mol %). The solution was stirred at room temperature for 30 minutes and then 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.01 mL, 6.94 mmol) was added dropwise, and the reaction was stirred overnight at room temperature. The next day, the reaction mixture was poured into water and the aqueous solution was extracted using ethyl acetate (3×). The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (silica gel, 50-80% ethyl acetate in dichloromethane) gave (2R,3S)-3-acetamido-N-tert-butyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)tetrahydrofuran-3-carboxamide as a colorless oil (864 mg, 63%). 1H NMR (CDCl3, 300 MHz) δ 7.01 (s, NH, 1 H), 6.10 (s, NH, 1 H), 4.38 (m, 1 H), 4.12 (m, 1 H), 4.00 (m, 1 H), 2.96 (m, 1 H), 2.02-2.18 (m, 2 H), 1.99 (s, 3 H), 1.42-1.62 (m, 3 H), 1.36 (s, 9 H), 1.22 (s, 12 H), 0.76 (m, 2 H); MS (+CI): m/z for C20H37BN2O5: expected 396.3; found 397.4 (M+H)+.

後処理

  1. stirringthe reaction was stirred overnight at room temperature
  2. extractionthe aqueous solution was extracted
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, 50-80% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-be95c65f74e34e7b897c3e04ec1a2c93
出典データセット
uspto-grants-2016_01
特許番号
US09233985B2

関連ノート

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