Triphenylphosphine → methyl 4-[3-[(E)-(1-benzylindol-3-yl)methylideneamino]oxypropoxy]-2-[(4-tert-butylbenzoyl)amino]benzoate

HRID 1392265Notes

Reaction equation

HRID 1392265 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[NH:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1.O[CH2:26][CH2:27][CH2:28][O:29][N:30]=[CH:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:26][CH2:27][CH2:28][O:29]/[N:30]=[CH:31]/[C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:33]=2)=[CH:6][C:5]=1[NH:11][C:12](=[O:23])[C:13]1[CH:14]=[CH:15][C:16]([C:19]([CH3:20])([CH3:21])[CH3:22])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 691962732-(4-Tert-butyl-benzoylamino)-4-hydroxy-benzoic acid methyl esterHCID 865983641-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oxime

Product 1

HCID 87729848methyl 4-[3-[(E)-(1-benzylindol-3-yl)methylideneamino]oxypropoxy]-2-[(4-tert-butylbenzoyl)amino]benzoateYield 55.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-tert-butyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester (0.313 g, 0.96 mmol) in tetrahydrofuran (14 mL) was added 1-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oxime (0.303 g, 0.98 mmol) and triphenyl phosphine (0.327 g, 1.26 mmol). The reaction was cooled to 0° C., diisopropyl azodicarboxylate (0.240 mL, 1.22 mmol) was added and warmed to room temperature overnight. It was poured into brine and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (10/90) to afford 4-[3-({[(1E)-(1-benzyl-1H-indol-3-yl)methylidene]amino}oxy)-propoxy]-2-[(4-tert-butylbenzoyl)amino]benzoic acid methyl ester (0.328g, 55 %) as a white solid. (+ES, M+H) m/z 618. 1H NMR (400 MHz, DMSO-d6); δ 11.95 (s, 1H), 8.42 (d, 1H), 8.38 (s, 1H), 7.98 (m, 2H), 7.88 (d, 2H), 7.82 (s, 1H) 7.62 (d, 2H), 7.47 (d, 1H), 7.29 (m, 2H), 7.21 (m, 4H), 7.08 (m, 1H), 6.81 (dd, 1H), 5.43 (s, 2H), 4.24 (m, 4H), 3.88 (s, 3H), 2.19 (m, 2H), 1.32 (s, 9H). Elemental analysis: Calcd. for C38H39N3O5: C, 73.88; H, 6.36; N, 6.8. Found: C, 73.40; H, 6.44; N, 6.37.

Workup

  1. temperaturewarmed to room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fdfea2d2bd6346dba1c93e73b0d41b27
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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