Dimethyl Sulfoxide → HCID 59200366、化合物

HRID 1685329ノート

反応式

HRID 1685329 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl.Cl>[O:11]=[CH:12][C:13]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59200464HCID 59200464、化合物

生成物 1

HCID 59200366HCID 59200366、化合物収率 87.5%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of oxalyl chloride (5.39 mL, 61.53 mmol) in dichloromethane (100 mL) was added dropwise dry DMSO (6.83 mL, 96.15 mmol) at −78° C. After 10 minutes at this temperature, a solution of benzyl 3-hydroxy-2,2-diphenylpropylcarbamate (13.9 g, 38.46 mmol) in dichloromethane (100 mL) was slowly added and stirred at −78° C. The reaction was stirred for 1 hour and triethylamine (26.8 mL, 192.3 mmol) was added and the reaction stirred at −78° C. for 10 more minutes then warmed to room 23° C. The reaction was diluted with 1N HCl and the phases were separated. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material (12.09 g, 87%) as an oil which was used as such in the next reaction. HPLC ret. time (Condition A): 2.093 min. LC/MS (M+H)+: 360. 1H NMR (400 MHz, CDCl3) δ ppm: 4.18 (2H, d, J=6.57 Hz), 4.98 (2H, s), 5.00 (1H, t, J=5.81 Hz), 7.17-7.42 (15H, 2 m), 9.90 (1H, s).

後処理

  1. stirringThe reaction was stirred for 1 hour
  2. stirringthe reaction stirred at −78° C. for 10 more minutes
  3. temperaturethen warmed to room 23° C
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-b83366e13dcc4de98a56f624084f8856
出典データセット
uspto-grants-2012_04
特許番号
US08148400B2

反応ノート

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