Trifluoroacetic acid → N-benzyl-O-benzyl-D-serinamide

HRID 534678

반응식

HRID 534678 반응식
[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([NH:8][C:9](=[O:28])[C@@H:10]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide

생성물 1

HCID 67082833N-benzyl-O-benzyl-D-serinamide수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (3 g) and dichloromethane (15 mL), trifluoroacetic acid (15 mL) was added. The solution was stirred for 2 hours at 40° C. for completion of reaction. The solution was concentrated under vacuum to remove solvents and subsequently water was added. The aqueous layer was basified to pH 8-10 with 5% sodium hydroxide. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue solidify by n-Hexane to give 1.55 g of N-benzyl-O-benzyl-D-serinamide.

후처리

  1. concentrationThe solution was concentrated under vacuum
  2. customto remove solvents and subsequently water
  3. additionwas added
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with brine solution
  6. concentrationOrganic layer was concentrated under vacuum
  7. customto obtain an oily residue solidify by n-Hexane

출처 및 근거

ORD 기록
ord-637b96a137da4747ae3a5d48b80551ca
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853439B2

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