Toluene → 2,4-bisbenzyloxy-N-butyl-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide

HRID 1927701Notes

Reaction equation

HRID 1927701 reaction equation
S(Cl)(Cl)=O.[CH3:5][N:6]([C:11]([C:13]1[C:14]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:15][C:16]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:17]([CH:21]=1)[C:18](O)=[O:19])=[O:12])[CH2:7][CH2:8][CH2:9][CH3:10].[C:38]1([CH3:44])[CH:43]=[CH:42]C=CC=1.[CH2:45]([N:47](C(C)C)C(C)C)C.[CH2:54]1C[O:57][CH2:56][CH2:55]1>ClCCl>[CH2:23]([O:22][C:16]1[CH:15]=[C:14]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:13]([C:11]([N:6]2[CH2:5][C:9]3[C:8](=[CH:54][CH:55]=[C:56]([OH:57])[CH:10]=3)[CH2:7]2)=[O:12])=[CH:21][C:17]=1[C:18]([N:47]([CH2:42][CH2:43][CH2:38][CH3:44])[CH3:45])=[O:19])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8028Tetrahydrofuran2×HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 596140605-[(N-Methyl-N-butylamino)carbonyl]-2,4-bisbenzyloxybenzoic acid

Product 1

HCID 596140942,4-bisbenzyloxy-N-butyl-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamideYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

652.9 μl (9 mmol) of thionyl chloride are added to a suspension of 2.06 g (4.6 mmol) of 2,4-bisbenzyloxy-5-[(N-methyl-N-butylamino) carbonyl]benzoic acid (5) in 20 ml of THF (dry), and the mixture is stirred for 15 min at 22° C. 10 ml of toluene are subsequently added, and the mixture is evaporated to dryness in vacuo at 40° C. The residue is dissolved in 20 ml of THF and added to a suspension of 800 mg (4.661 mmol) of 2,3-dihydro-1H-isoindol-5-ole hydrochloride in 30 ml of dichloromethane, 5 ml of THF and 1.7 ml (10 mmol) of N-ethyldiisopropylamine. After 2 h at 22° C., the mixture is evaporated and chromatographed over an RP18 column. Evaporation to dryness in vacuo gives 1.4 g (54%) of 2,4-bisbenzyloxy-N-butyl-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide as beige crystals, MW 564.7;

Workup

  1. customthe mixture is evaporated to dryness in vacuo at 40° C
  2. dissolutionThe residue is dissolved in 20 ml of THF
  3. waitAfter 2 h at 22° C.
  4. customthe mixture is evaporated
  5. customchromatographed over an RP18 column
  6. customEvaporation to dryness in vacuo

Sources & evidence

ORD record
ord-94a52d0c19b848808807054dc9e2cf74
Source dataset
uspto-grants-2012_05
Patent number
US08183279B2

Reaction notes

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