Sodium Hydroxide → HCID 58043136、化合物

HRID 1035170ノート

反応式

HRID 1035170 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([OH:18])[CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CS(O[CH:24]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25]1)(=O)=O.[OH-].[Na+]>CN(C=O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[O:18][CH:24]1[CH2:25][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateHCID 580431463-Methoxy-4-(morpholinomethyl)phenol

生成物 1

HCID 58043136HCID 58043136、化合物収率 105.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
80 °C

実験手順

A mixture of NaH (55-65% disp. in oil, 0.30 g, 6.88 mmol) in dry DMF (5 mL) under nitrogen was cooled by a water-bath. A solution of 7A (1.17 g, 5.24 mmol) in DMF (10 mL) was added drop-wise over 15 minutes. The mixture was stirred for one h and then tert-butyl 3-[(methylsulfonyl)oxy]azetidine-1-carboxylate (1.7 g, 6.77 mmol) in DMF (10 mL) was added. The mixture was heated to 80° C. for 3 days and then cooled to RT. Water and some aqueous NaOH were added and the mixture was extracted three times with EtOAc. The combined organic solutions were dried (MgSO4) and evaporated. The residue was purified by column chromatography on SiO2 using 5% triethylamine in EtOAc as eluent. There was obtained 2.1 g (104%) of 7B as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 1.45 (s, 9H), 2.39-2.56 (m, 4H), 3.48 (s, 2H), 3.65-3.75 (m, 4H), 3.79 (s, 3H), 3.95-4.04 (m, 2H), 4.23-4.33 (m, 2H), 4.82-4.91 (m, 1H), 6.19 (d, 1H), 6.38 (s, 1H), 7.21 (d, 1H).

後処理

  1. temperaturewas cooled by a water-bath
  2. temperaturecooled to RT
  3. extractionthe mixture was extracted three times with EtOAc
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on SiO2 using 5% triethylamine in EtOAc as eluent

出典と根拠

ORDレコード
ord-c778325494ed4aeab2275a5d00a2f54c
出典データセット
uspto-grants-2013_10
特許番号
US08546375B2

反応ノート

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