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

HRID 1678511Notes

Reaction equation

HRID 1678511 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[CH2:31][CH2:30][CH2:29][C@@H:28]1[C:32](O)=[O:33])([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[CH2:31][CH2:30][CH2:29][C@@H:28]1[C:32](=[O:33])[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 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-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 67374244(R)-2-(6-Chloro-4'-ethoxycarbonyl-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-amino-2′-chloro-biphenyl-4-carboxylic acid ethyl ester (800 mg), (R) —N-Boc-2-pyrrolidinecarboxylic acid (608 mg) and HBTU (1.46 g) in dry DMF (30 ml) containing N-methylmorpholine (1.26 ml) was stirred at room temp for 18 h. Silica gel (5 g) was then added and the mixture evaporated. The residue was purified by chromatography. Elution with 12:1 petrol:ethyl acetate gave a viscous brown gum (987 mg)

Workup

  1. additionSilica gel (5 g) was then added
  2. customthe mixture evaporated
  3. customThe residue was purified by chromatography
  4. washElution with 12:1 petrol

Sources & evidence

ORD record
ord-2a585386445846e38c8bd26c633fbfcc
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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