Triethylamine → (2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-hydroxy-7-methyl-1,3-dihydro-isoindol-2-yl)-methanone

HRID 1625402Notes

Reaction equation

HRID 1625402 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=N)C.ON1C2C=CC=CC=2N=N1.Br.[CH3:46][C:47]1[CH:48]=[C:49]([OH:56])[CH:50]=[C:51]2[C:55]=1[CH2:54][NH:53][CH2:52]2.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([N:53]1[CH2:52][C:51]2[C:55](=[C:47]([CH3:46])[CH:48]=[C:49]([OH:56])[CH:50]=2)[CH2:54]1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 21883477Ethylcarbodiimide hydrochlorideHCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acidHCID 666720887-methyl-2,3-dihydro-1H-isoindol-5-ol hydrobromide

Product 1

HCID 59263143(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-hydroxy-7-methyl-1,3-dihydro-isoindol-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Bis-benzyloxy-5-isopropenyl-benzoic acid (248 mg, 0.66 mmol), 1-[3-(dimethylamino)propyl)]-3-ethylcarbodiimide hydrochloride (127 mg, 0.66 mmol) and 1-hydroxybenztriazole (89 mg, 0.66 mmol) were dissolved in DMF (5 mL). After 20 minutes, 7-methyl-2,3-dihydro-1H-isoindol-5-ol hydrobromide (152 mg, 0.66 mmol) and triethylamine (0.14 mL, 0.99 mmol) were added. After a further 3.5 hours the mixture was concentrated in vacuo and the residue was treated with 1N hydrochloric acid and ethyl acetate. The aqueous phase was removed, brine was added and the title compound was collected by filtration as a grey solid (168 mg, 57%). 1H NMR (DMSO-d6) 9.30 (0.47H, s), 9.24 (0.53H, s), 7.48-7.25 (10H, m), 7.09 (0.47H, s), 7.08 (0.53H, s), 6.99 (0.47H, s), 6.98 (0.53H, s), 6.56 (0.47H, s), 6.50 (0.53H, s), 6.48 (0.47H, s), 6.44 (0.53H, s), 5.24 (0.47H, s), 5.22 (0.53, s), 5.18 (2H, s), 5.10-5.07 (2H, m), 4.70 (0.47H, s), 4.61 (0.53H, s), 4.46 (0.47H, s), 4.36 (0.53H, s), 2.17 (1.41H, s), 2.04 (3H, s), 1.99 (1.59H, s). MS: [M+H]+ 506.

Workup

  1. concentrationAfter a further 3.5 hours the mixture was concentrated in vacuo
  2. additionthe residue was treated with 1N hydrochloric acid and ethyl acetate
  3. customThe aqueous phase was removed
  4. additionbrine was added
  5. filtrationthe title compound was collected by filtration as a grey solid (168 mg, 57%)

Sources & evidence

ORD record
ord-dce3b8992f5447199d364c0ddcd92311
Source dataset
uspto-grants-2014_07
Patent number
US08779132B2

Reaction notes

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