Sodium Hydroxide → HCID 11157733, compound

HRID 1392266Notes

Reaction equation

HRID 1392266 reaction equation
C[O:2][C:3](=[O:46])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:18]=2)=[CH:6][C:5]=1[NH:33][C:34](=[O:45])[C:35]1[CH:40]=[CH:39][C:38]([C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:37][CH:36]=1.[OH-].[Na+]>C(O)C.O.O1CCCC1>[CH2:26]([N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](/[CH:16]=[N:15]/[O:14][CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:46])=[O:2])=[C:5]([NH:33][C:34](=[O:45])[C:35]3[CH:36]=[CH:37][C:38]([C:41]([CH3:43])([CH3:42])[CH3:44])=[CH:39][CH:40]=3)[CH:6]=2)=[CH:18]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87729848methyl 4-[3-[(E)-(1-benzylindol-3-yl)methylideneamino]oxypropoxy]-2-[(4-tert-butylbenzoyl)amino]benzoate

Product 1

HCID 11157733HCID 11157733, compound

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of 4-[3-({[(1E)-(1-benzyl-1H-indol-3-yl)methylidene]amino}oxy)-propoxy]-2-[(4-tert-butylbenzoyl)amino]benzoic acid methyl ester (0.229 g, 0.47 mmol) in ethanol/water/tetrahydrofuran (8/3/1) was added 2.5 N NaOH (6 mL, 15 mmol) and the reaction was heated at reflux for 45 minutes until all starting material was gone. It was cooled to room temperature, concentrated to a small volume in vacuo and acidified to pH 1 with 2N HCl solution. It was extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (10/90 to 20/80) to the title compound (0.200 g, 70%) as an off-white solid. mp=180.9-182.5° C. mass spectrum (+ES, M+H) m/z 604. 1H NMR (400 MHz, DMSO-d6); δ 13.40 (bs, 1H), 12.40 (bs, 1H), 8.65 (d, 1H), 8.39 (s, 1H), 7.98 (d, 2H), 7.87 (d, 2H), 7.82 (s, 1H) 7.60 (d, 2H), 7.48 (d, 1H), 7.30 (m, 2H), 7.2-2 (m, 4H), 7.09 (m, 1H), 6.78 (dd, 1H), 5.42 (s, 2H), 4.26 (t, 2H), 4.22 (t, 2H), 2.20 (m, 2H), 1.31 (s, 9H) Elemental analysis: Calcd. for C37H37N3O5: C, 73.61; H, 6.18; N, 6.96. Found: C, 72.91; H, 6.22; N, 6.70.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 45 minutes until all starting material
  3. concentrationconcentrated to a small volume in vacuo
  4. extractionIt was extracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4788fadc614a4dc6b97e197fcde919f4
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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