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

HRID 1185468Notes

Reaction equation

HRID 1185468 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-964764418fad42b381aa678a45537da8
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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