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

HRID 225963
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HRID 225963 반응식
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
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7

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

생성물 1

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

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
3회
HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

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%

후처리

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

출처 및 근거

ORD 기록
ord-6dd253af78784f58a4b7a95384746900
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557136B2

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