4-Methylmorpholine → (R)-2-(6-Chloro-4'-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1678514Notes

Reaction equation

HRID 1678514 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[C:20]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]1[C:33](O)=[O:34])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:23]([O:22][C:20]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@@H:28]1[C:33](=[O:34])[NH:18][C:16]1[CH:17]=[C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[C:13]([Cl:19])=[CH:14][CH:15]=1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 688618(2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 598223745'-Amino-2'-chloro-biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 67372169(R)-2-(6-Chloro-4'-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl esterYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-amino-2′-chloro-biphenyl-4-carboxylic acid ethyl ester (750 mg), (R)-N-Boc-2-piperidinecarboxylic acid (664 mg) and HBTU (1.37 g) in dry DMF (40 ml) containing N-methylmorpholine (1.2 ml) was stirred at room temp for 18 h. The mixture was then evaporated and the residue was purified by chromatography. Elution with 5:1 petrol:ethyl acetate gave a yellow oil (310 mg)

Workup

  1. customThe mixture was then evaporated
  2. customthe residue was purified by chromatography
  3. washElution with 5:1 petrol

Sources & evidence

ORD record
ord-7f1485689fb44103b1e24a63a77d97a0
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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