Dimethylformamide → HCID 117697690、化合物

HRID 1778478ノート

反応式

HRID 1778478 の反応式
CC([O-])(C)C.[K+].[C:7](=O)([O:10]C)[O:8][CH3:9].[C:13]([O:17][C:18]([N:20]1[CH:25]2[CH2:26][C:27](=[O:29])[CH2:28][CH:21]1[CH2:22][O:23][CH2:24]2)=[O:19])([CH3:16])([CH3:15])[CH3:14].CN(C=O)C>C1(C)C=CC=CC=1>[CH3:9][O:8][C:7]([CH:26]1[C:27](=[O:29])[CH2:28][CH:21]2[N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])[CH:25]1[CH2:24][O:23][CH2:22]2)=[O:10]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 12021Dimethyl CarbonateHCID 185070529-Boc-7-oxa-9-azabicyclo[3.3.1]nonan-3-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 117697690HCID 117697690、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a suspension of t-BuOK (1.82 g, 16.26 mmol) in toluene (30 mL) was added dimethyl carbonate (0.98 g, 10.84 mmol). The mixture was heated at 90° C. for 5 mins, and then 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (1.3 g, 5.4 mmol) was added. After the resulting mixture was stirred at 90° C. for 30 mins, the mixture was turned to brown gel, and then DMF (1.5 mL) was added to get a brown solution. The mixture was stirred at 90° C. for 3 hours. After it was cooled to room temperature, silica gel (25 g, 100200 mesh) was added and the solvent was concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc in PE 0%˜70%) to give 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-6,9-dicarboxylic acid 9-tert-butyl ester 6-methyl ester (Compound AO) as light yellow oil (0.8 g, 49%). LC/MS: calc'd 300 (MH+), exp 300 (MH+); 1HNMR (400 MHz, CDCl3) δ 1.40-1.45 (m, 9H), 2.29-2.41 (m, 1H), 2.68-2.84 (m, 1H), 3.47-3.79 (m, 7H), 3.88-3.96 (m, 0.5H), 4.09-4.16 (m, 0.3H), 4.30-4.45 (m, 1H), 4.55-4.67 (m, 0.8H), 11.86 (s, 0.3H).

後処理

  1. customto get a brown solution
  2. stirringThe mixture was stirred at 90° C. for 3 hours
  3. temperatureAfter it was cooled to room temperature
  4. additionsilica gel (25 g, 100200 mesh) was added
  5. concentrationthe solvent was concentrated in vacuo
  6. customThe residue was purified by flash column chromatography (EtOAc in PE 0%˜70%)

出典と根拠

ORDレコード
ord-f0bc95a41ac749d2aa176bdb86f1dc12
出典データセット
uspto-grants-2016_02
特許番号
US09266904B2

反応ノート

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