Benzoic Acid → HCID 131724566, compound

HRID 1837279Notes

Reaction equation

HRID 1837279 reaction equation
[CH2:1]([C@@H:11]1[CH2:28][C:27]2[CH:26]=[C:25]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:24]=[CH:23][C:22]=2[C@@H:21]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:20]2[F:37])([CH3:18])[C:16](=[O:38])[CH2:15][CH2:14]1)[CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:39]([OH:47])(=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C>CN(C)C=O>[CH2:30]([O:29][C:25]1[CH:24]=[CH:23][C:22]2[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][C@@H:20]3[F:37])([CH3:18])[C:16](=[O:38])[CH2:15][CH2:14]4)[C@H:11]([CH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:39](=[O:47])[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:28][C:27]=2[CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 69916367HCID 69916367, compound

Product 1

HCID 131724566HCID 131724566, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 275 mg of 7α-(5-azadecyl)-3-benzyloxy-11β-fluor-estra-1,3,5(10)-trien-17-one in 7.8 ml of dimethylformamide is stirred with 175 mg of benzoic acid and 250 mg of 1-hydroxybenzotriazole and 0.2 ml of N,N′-diisopropylcarbodiimide for 24 hours at room temperature. Then, the reaction mixture is added to ice water, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a methylene chloride-methanol gradient, 197 mg of N-[4-(3-benzyloxy-11β-fluor-estra-1,3,5(10)-trien-17-on-7α-yl)-butyl)-N-pentyl-benzamide is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated by evaporation in a vacuum
  5. customAfter the crude product is chromatographed on silica gel with a methylene chloride-methanol gradient

Sources & evidence

ORD record
ord-034aed33758e4d7190cca94b976c2f1e
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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