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L-Serine → (2S)-3-Hydroxy-2-[(triphenylmethyl)amino]propanoic acid

HRID 80323
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HRID 80323 반응식
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C[Si](Cl)(C)C.C(N(CC)CC)C.[C:20]1([C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)Cl)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.CO>[C:20]1([C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 5951L-SerineHCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 8471Triethylamine2회

생성물 1

HCID 10991634(2S)-3-Hydroxy-2-[(triphenylmethyl)amino]propanoic acid수율 5.2%

시약·촉매·용매 2

HCID 887Methanol
용매
2회
HCID 6344Dichloromethane용매

실험 절차

L-Serine (2.10 g, 20.0 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in methylene chloride (20 mL) (Wako Pure Chemical Industries, Ltd.), and then trimethylsilyl chloride (8.9 mL) (Shin-Etsu Chemical Co., Ltd.) was added thereto, followed by reflux for 20 minutes. The mixture was returned to room temperature, and then triethylamine (10 mL) (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by reflux for 45 minutes. The mixture was ice-cooled, and then triethylamine (2.8 mL) (Wako Pure Chemical Industries, Ltd.) and triphenylchloromethane (5.61 g, 20.1 mmol) (Wako Pure Chemical Industries, Ltd.) were added thereto, followed by stirring at room temperature for 5 hours. An excessive amount of methanol (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution, and the mixture was concentrated under reduced pressure. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=99:1 as an eluent), to thereby obtain the title compound (0.36 g, 5% yield).

후처리

  1. temperatureby reflux for 20 minutes
  2. customwas returned to room temperature
  3. temperatureby reflux for 45 minutes
  4. temperaturecooled
  5. concentrationthe mixture was concentrated under reduced pressure
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-b916d736b4584acab21f7f7a32f08400
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846012B2

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