Dichloromethane → N-benzyl-O-benzyl-D-serinamide

HRID 534679

반응식

HRID 534679 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.ClCCl.FC(F)(F)C(O)=O.[OH-].[Na+]>O>[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

6

반응물 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 7216909N-benzyl-O-benzyl-N2-Boc-D-serinamide

생성물 1

HCID 67082833N-benzyl-O-benzyl-D-serinamide수율 90.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of N-benzyl-O-benzyl-N2-Boc-D-serinamide (30 g) and dichloromethane (150 mL), trifluoroacetic acid (150 mL) was added. The solution was stirred for 2 hours at room temperature for completion of reaction. The solution was concentrated under vacuum to obtain solid which was dissolved in water. 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 layers washed with brine solution. Organic layer was concentrated under vacuum to obtain an oily residue solidify by n-Hexane to give 20 g of N-benzyl-O-benzyl-D-serinamide.

후처리

  1. concentrationThe solution was concentrated under vacuum
  2. customto obtain solid which
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers washed with brine solution
  5. concentrationOrganic layer was concentrated under vacuum
  6. customto obtain an oily residue solidify by n-Hexane

출처 및 근거

ORD 기록
ord-be2f9f7a3be14f24980bc1a11043ee1e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853439B2

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