1-Piperazinecarboxylic acid, ethyl ester → 4-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1185444

반응식

HRID 1185444 반응식
[C:1]([O:5][C:6](=[O:23])[CH2:7][C@H:8]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:46]([O:48][C:49]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)=[O:50])[CH3:47].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:46]([O:48][C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:9](=[O:11])[C@@H:8]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:23])[CH2:55][CH2:56]1)=[O:50])[CH3:47]

참가 물질

6

반응물 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 669202694-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 25 g of (S)-2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester, 35.6 g of NEM and 25.3 g of TOTU in 125 ml of DMF, 12.9 g of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 3 h. The reaction mixture was diluted saturated aqueous sodium hydrogen carbonate solution and extracted with 400 ml of ethyl acetate. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1). The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 35.4 g.

후처리

  1. extractionextracted with 400 ml of ethyl acetate
  2. washThe organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1)
  6. additionThe fractions containing the product
  7. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-a353c04b1cfd4b909f7c6f2e9469fe64
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669266B2

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