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

HRID 1185528Notes

Reaction equation

HRID 1185528 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:47][C:48]([N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)=[O:49])[CH3:46]>C(OCC)(=O)C>[CH2:45]([O:47][C:48]([N:50]1[CH2:51][CH2:52][N:53]([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][CH2:55]1)=[O:49])[CH3:46]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13105160(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-fluoropropanoic acid

Product 1

HCID 686001074-((R)-2-tert-Butoxycarbonylamino-3-fluoro-propionyl)-piperazine-1-carboxylic acid ethyl 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-ethoxycarbonylpiperazine. 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: 160 mg.

Workup

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

Sources & evidence

ORD record
ord-b7e0609d1710482394f153028f397fd9
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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