Toluene → HCID 89964223, compound

HRID 626323Notes

Reaction equation

HRID 626323 reaction equation
C([NH:8][C:9](=[O:42])[C@@H:10]([N:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[CH:30][CH:29]=2)[C:18]1=[O:41])[CH2:11][CH2:12][C:13](OC)=[O:14])C1C=CC=CC=1.[C:43]1([CH3:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:49]([N:8]1[C:13](=[O:14])[CH2:12][CH2:11][C@H:10]([N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[CH:30][CH:29]=3)[C:18]2=[O:41])[C:9]1=[O:42])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 89964676HCID 89964676, compound

Product 1

HCID 89964223HCID 89964223, compound

Procedure

A mixture of (S)-methyl 5-(benzylamino)-4-(4-((4-(morpholinomethyl)benzyl)oxy)-1-oxoisoindolin-2-yl)-5-oxopentanoate (2.5 mmol) and p-TsOH monohydrate (1.25 mmol) in toluene, under argon, is refluxed for 8 hours. The solvent is evaporated. The crude is taken up in ether (50 mL) and washed with saturated aqueous NaHCO3 (2×20 mL). The organic layer is dried and purified by silica gel chromatography to afford (S)-1-benzyl-3-(4-((4-(morpholinomethyl)benzyl)oxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione.

Workup

  1. temperatureunder argon, is refluxed for 8 hours
  2. customThe solvent is evaporated
  3. washwashed with saturated aqueous NaHCO3 (2×20 mL)
  4. customThe organic layer is dried
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-496e120a24fd431bbbd3dd37fb9d7470
Source dataset
uspto-grants-2016_04
Patent number
US09309220B2

Reaction notes

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