Succinic anhydride → HCID 131728230, compound

HRID 20932Notes

Reaction equation

HRID 20932 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[O:10][CH:11]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:12]2[CH2:16][CH:15]([OH:17])[CH2:14][N:13]2[C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:5][CH:4]=1.[C:42]1(=[O:48])[O:47][C:45](=[O:46])[CH2:44][CH2:43]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[O:10][CH:11]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:12]2[N:13]([C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[CH2:14][CH:15]([O:17][C:42](=[O:48])[CH2:43][CH2:44][C:45]([OH:47])=[O:46])[CH2:16]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131728231HCID 131728231, compound

Product 1

HCID 131728230HCID 131728230, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 25, Compound 94 (1.2 g, 2 mmol) is mixed with succinic anhydride (0.200 g, 2 mmol) and DMAP (0.244 g, 13 mmol) and dried in a vacuum at 40° C. overnight. The mixture is dissolved in anhydrous dichloromethane (5 mL), triethylamine (0.476 g, 0.64 mL, 4 mmol) is added and the solution stirred at room temperature under argon atmosphere for 16 h. It is then diluted with dichloromethane (100 mL) and washed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 mL). The organic phase is dried over anhydrous sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography to afford compound 96.

Workup

  1. customdried in a vacuum at 40° C. overnight
  2. dissolutionThe mixture is dissolved in anhydrous dichloromethane (5 mL)
  3. washwashed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 mL)
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-16b740aa069045dfa087254611dd33b4
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

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