Ethylmorpholine → 4-((R)-2-tert-Butoxycarbonylamino-3-fluoro-propionyl)-piperazine-1-carboxylic acid butyl ester

HRID 1185530Notes

Reaction equation

HRID 1185530 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][F:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:45]([O:49][C:50]([N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)=[O:51])[CH2:46][CH2:47][CH3:48]>C(OCC)(=O)C>[CH2:45]([O:49][C:50]([N:52]1[CH2:57][CH2:56][N:55]([C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][F:14])[CH2:54][CH2:53]1)=[O:51])[CH2:46][CH2:47][CH3:48]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13105160(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-fluoropropanoic acidHCID 21963126Butyl piperazine-1-carboxylate

Product 1

HCID 685998364-((R)-2-tert-Butoxycarbonylamino-3-fluoro-propionyl)-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 150 mg (R)-2-tert-Butoxycarbonylamino-3-fluoro-propionic acid were added 0.18 ml N-ethylmorpholine, 237 mg TOTU and 115 mg 1-butoxycarbonylpiperazine. After stirring for 12 h the reaction mixture was diluted with ethyl acetate and washed with aqueous LiCl (4%), 0.1 M HCl, saturated aqueous NaHCO3 and brine. The crude product obtained was used without further purification. Yield: 230 mg.

Workup

  1. washwashed with aqueous LiCl (4%), 0.1 M HCl, saturated aqueous NaHCO3 and brine

Sources & evidence

ORD record
ord-e2f9b85c0f4a463a930a1a3dc7ff410a
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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