4-Methylmorpholine → 5'-[2-(tert-Butoxycarbonyl-methyl-amino)-acetylamino]-2'-chloro-biphenyl-4-carboxylic acid ethyl ester

HRID 1678517Notes

Reaction equation

HRID 1678517 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]([O:24][C:25]([N:27]([CH2:29][C:30](O)=[O:31])[CH3:28])=[O:26])([CH3:23])([CH3:22])[CH3:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH:18][C:30](=[O:31])[CH2:29][N:27]([C:25]([O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:26])[CH3:28])[CH:15]=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 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 673712285'-[2-(tert-Butoxycarbonyl-methyl-amino)-acetylamino]-2'-chloro-biphenyl-4-carboxylic acid ethyl esterYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-amino-2′-chloro-biphenyl-4-carboxylic acid ethyl ester (750 mg), (tert-butoxycarbonyl-methyl-amino)-acetic acid (589 mg) and HBTU (1.37 g) in dry DMF (40 ml) containing N-methylmorpholine (0.79 ml) was stirred at room temp for 18 h. The mixture was then evaporated and the residue was purified by chromatography. Elution with 4:1 petrol:ethyl acetate gave a pale brown oil (494 mg)

Workup

  1. customThe mixture was then evaporated
  2. customthe residue was purified by chromatography
  3. washElution with 4:1 petrol

Sources & evidence

ORD record
ord-9d5fbf08eb4f49e7985984621f480f3d
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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