Sodium Bicarbonate → 4-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-piperazine-1-carboxylic acid butyl ester

HRID 1185468노트

반응식

HRID 1185468 반응식
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.FC(F)(F)C(O)=O.[CH2:52]([O:56][C:57]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)=[O:58])[CH2:53][CH2:54][CH3:55].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:52]([O:56][C:57]([N:59]1[CH2:64][CH2:63][N:62]([C:12](=[O:14])[C@@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:61][CH2:60]1)=[O:58])[CH2:53][CH2:54][CH3:55]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserineHCID 66854479Piperazine-1-carboxylic acid butyl ester trifluoroacetate

생성물 1

HCID 685989064-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-piperazine-1-carboxylic acid butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5 g of (S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid, 7.4 g of NEM and 5.3 g of TOTU in 35 ml of DMF, 4.8 g of Piperazine-1-carboxylic acid butyl ester trifluoroacetate was added at RT and stirred for 16 h. The reaction mixture was diluted saturated aqueous sodium hydrogen carbonate solution and extracted with 250 ml of ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 6.3 g.

후처리

  1. extractionextracted with 250 ml of ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-964764418fad42b381aa678a45537da8
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669266B2

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