Triethylamine → (2R,4R)-7-biphenyl-4-ylmethyl-2,4-dimethyl-6-oxo-nonanedioic acid 9-tert-butyl ester 1-ethyl ester

HRID 70849Notes

Reaction equation

HRID 70849 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH:26]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[CH2:54]([O:56][C:57](=[O:64])[C@H:58]([CH3:63])[CH2:59][C@H:60](N)[CH3:61])[CH3:55].C(N(CC)CC)C>CN(C=O)C>[CH2:54]([O:56][C:57](=[O:64])[C@H:58]([CH3:63])[CH2:59][C@@H:60]([CH3:26])[CH2:61][C:9](=[O:10])[CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:25])[CH3:55]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 596078262-Biphenyl-4-ylmethyl-succinic acid 4-tert-butyl esterHCID 86648194(2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate

Product 1

HCID 68424555(2R,4R)-7-biphenyl-4-ylmethyl-2,4-dimethyl-6-oxo-nonanedioic acid 9-tert-butyl ester 1-ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester (100 mg, 0.29 mmol) in DMF (10 mL) is added HOBt (45 mg, 0.29 mmol) and EDCI (56 mg, 0.29 mmol) and the mixture is stirred at room temperature for 10 minutes then (2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate (47 mg, 0.29 mmol) and triethylamine (89 mg, 0.87 mmol) is added and the mixture is stirred at room temperature for 5 hours. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure to give (2R,4R)-7-biphenyl-4-ylmethyl-2,4-dimethyl-6-oxo-nonanedioic acid 9-tert-butyl ester 1-ethyl ester.

Workup

  1. stirringthe mixture is stirred at room temperature for 5 hours
  2. customThe mixture is quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-2bd8aac4f5a643339cc33e6c7c6d2f2f
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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