1-Hydroxybenzotriazole → 2-hydroxy-8-phenyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)octanamide

HRID 445394Notes

Reaction equation

HRID 445394 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([OH:5])=O.C(O)(=O)C(O)=O.[C:24]1([C:30]2[O:34][C:33]([CH2:35][NH2:36])=[N:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([NH:36][CH2:35][C:33]1[O:34][C:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:31][N:32]=1)=[O:5]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45925648(5-Phenyl-1,3,4-oxadiazol-2-yl)methanamine oxalateHCID 537335152-Hydroxy-8-phenyloctanoic acid

Product 1

HCID 668222512-hydroxy-8-phenyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)octanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-8-phenyloctanoic acid (458 mg, 1.94 mmol), 5-phenyl-1,3,4-oxadiazol-2-yl methanamine oxalate (514 mg, 1.94 mmol), HOBt (314 mg, 2.3 mmol) and diisopropylethyl amine (501 mg, 3.9 mmol) in DMF (15 mL) was added 1-ethyl-3(3-dimethylaminopropyl) carbodiimide hydrochloride (446 mg, 2.3 mmol). The suspension was stirred for 48 h then filtered. The filtrate was diluted with EtOAc and washed sequentially with water, saturated NaHCO3, and brine. The organic phase was dried (Na2SO4) and filtered and the residue triturated with EtOAc to yield 2-hydroxy-8-phenyl-N-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)octanamide (MH+=394).

Workup

  1. filtrationthen filtered
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed sequentially with water, saturated NaHCO3, and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe residue triturated with EtOAc

Sources & evidence

ORD record
ord-58726b9c410d457bb9ef4c7b17f6a3c0
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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