4-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartate → 4-((S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1908650Notes

Reaction equation

HRID 1908650 reaction equation
[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)=N[O:36][C:37]([N:41]([CH3:43])[CH3:42])=[N+](C)C)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:5][C:37]([N:41]1[CH2:42][CH2:13][N:12]([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])[CH2:8][CH2:43]1)=[O:36])[CH3:2]

Participants

5

Reactant 2

HCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 15.4 g (S)-2-Benzyloxycarbonylamino-succinic acid 4-tert-butyl ester, 24.4 ml NEM and 15.6 g TOTU in 80 ml DMF 7.5 g piperazine-1-carboxylic acid ethyl ester were added at RT and stirred for 16 h. The reaction mixture was then diluted with ethyl acetate and washed with aqueous LiCl (4 w/w) and saturated aqueous sodium hydrogen carbonate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was used in the subsequent reaction. Yield: 23.0 g.

Workup

  1. washwashed with aqueous LiCl (4 w/w) and saturated aqueous sodium hydrogen carbonate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was used in the subsequent reaction

Sources & evidence

ORD record
ord-390c5f15dc7441ce99ae0e6296d58905
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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