Triethylamine → benzoic acid N'-[2-(2-sec-butyl-phenoxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250936

Reaction equation

HRID 2250936 reaction equation
[CH:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([OH:11])=O)([CH2:3][CH3:4])[CH3:2].[CH:16]([NH:19][NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:18])[CH3:17].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([N:19]([CH:16]([CH3:18])[CH3:17])[NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:11])([CH2:3][CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 188691-Benzoyl-2-isopropylhydrazineHCID 757711-HydroxybenzotriazoleHCID 3365714(2-Sec-butylphenoxy)acetic acid

Product 1

HCID 11566858benzoic acid N'-[2-(2-sec-butyl-phenoxy)-acetyl]-N'-isopropyl-hydrazideYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2-sec-butyl-phenoxy)-acetic acid (193 mg, 0.93 mmol), and benzoic acid N′-isopropyl-hydrazide (150 mg, 0.842 mmol) in DMF (5 ml), was treated with triethylamine (0.352 ml, 2.52 mmol), HOBT (136 mg, 1.00 mmol), and EDCI (194 mg, 1.00 mmol) for 12 hours at room temperature. The reaction mixture was partitioned between 1N HCl and DCM. The organic layer was successively washed with 1N NaOH and brine, then dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with 50% ethyl acetate/hexanes to afford the product as a white solid (113 mg, 33%). MS m/e 369.32 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and DCM
  2. washThe organic layer was successively washed with 1N NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fcb937a1d1344f42b2833a0eaa607652
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Linked notes

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