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Dimethyl Sulfoxide → methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate

HRID 225963
ノート
印刷プレビュー

反応式

HRID 225963 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:16]=[CH:15][C:14]([C:17]([N:19]2[CH2:23][C@H:22]([OH:24])[CH2:21][C@H:20]2[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:11]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]=[CH:13][C:14]([C:17]([N:19]2[CH2:23][C:22](=[O:24])[CH2:21][C@H:20]2[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:18])=[CH:15][CH:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86760912methyl [(2S,4R)-1-(biphenyl-4-ylcarbonyl)-4-hydroxypyrrolidin-2-yl]acetate

生成物 1

HCID 86760911methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate収率 130.4%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
3 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

A solution of DMSO (31.4 μl, 0.44 mmol) in dichloromethane (1 ml) was added drop wise to a solution of oxalyl chloride (19 μl, 0.22 mmol) in dichloromethane (2 ml) at −78° C. under argon. After 15 min at −78° C., A solution of methyl [(2S,4R)-1-(biphenyl-4-ylcarbonyl)-4-hydroxypyrrolidin-2-yl]acetate (50 mg, 0.15 mmol) in dichloromethane (1 ml) was added drop wise. The reaction mixture was stirred at −78° C. for 1 hour and triethylamine (0.102 ml, 0.74 mmol) was added and allowed to warm to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water then brine. The organic phase was dried (MgSO4) and concentrated to afford the methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate (66 mg). Yield: 100%. HPLC purity: 99%

後処理

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-6dd253af78784f58a4b7a95384746900
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557136B2

反応ノート

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