Dimethylformamide → HCID 66671331, compound

HRID 2371111Notes

Reaction equation

HRID 2371111 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN1CC[O:15][CH2:14]C1.O[C:19]1[C:27]2N=NN[C:23]=2[CH:22]=[CH:21][CH:20]=1.C(OC(NC[CH2:40][CH:41]([CH:49]([OH:64])[CH2:50][CH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:54][CH:53]=1)[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=O)C1C=CC=CC=1.C(N=C=NCCCN(C)C)C.C[N:77]([CH3:80])C=O>O>[C:14]([O:64][CH:49]([CH2:50][CH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[CH:54][CH:53]=1)[CH:41]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH2:80][NH:77][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=1)(=[O:15])[C:19]1[CH:27]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 99734-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66671372HCID 66671372, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 66671331HCID 66671331, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Fluorobenzoic acid (45 mg), N-methylmorpholine (0.05 ml), hydroxybenzotriazole (51.5 mg) were added to the solution of 4-amino-1-(2-biphenyl-4-ylethyl)-2-(tert-butoxycarbonyl)butyl benzoate (150 mg) obtained from Example 3, step 2 in dry dimethylformamide (2 ml) at 0° C., 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide (92 mg) was added and the reaction mixture was stirred overnight. The reaction mixture was taken in distilled water and extracted with ethylacetate. The organic layer was washed with distilled water and brine solution and dried over anhydrous sodium sulphate followed by evaporation under reduced pressure. The residue thus obtained was purified by column chromatography using 10% ethyl acetate in hexane as eluent to get the title compound (120 mg).

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with distilled water and brine solution
  3. dry with materialdried over anhydrous sodium sulphate
  4. customfollowed by evaporation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-93f507d4bfcc46cfbeadc17cd5d27ec5
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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