Succinic anhydride → HCID 131728208, compound

HRID 2402994Notes

Reaction equation

HRID 2402994 reaction equation
[CH3:1][C:2]12[CH2:18][CH2:17][CH:16]([O:19][C:20](=[O:60])[NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]3[CH2:33][CH:32]([OH:34])[CH2:31][CH:30]3[CH:35]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[O:36][CH:37]([C:46]3[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=3)[C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)=[O:28])[CH2:15][C:14]1=[CH:13][CH2:12][CH:11]1[CH:3]2[CH2:4][CH2:5][C:6]2([CH3:69])[CH:10]1[CH2:9][CH2:8][CH:7]2[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68].[C:70]1(=[O:76])[O:75][C:73](=[O:74])[CH2:72][CH2:71]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:53][O:52][C:49]1[CH:50]=[CH:51][C:46]([CH:37]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[O:36][CH:35]([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:30]2[N:29]([C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:20]([O:19][CH:16]3[CH2:15][C:14]4[C:2]([CH3:1])([CH:3]5[CH:11]([CH2:12][CH:13]=4)[CH:10]4[C:6]([CH3:69])([CH:7]([CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])[CH2:8][CH2:9]4)[CH2:5][CH2:4]5)[CH2:18][CH2:17]3)=[O:60])[CH2:33][CH:32]([O:34][C:70](=[O:76])[CH2:71][CH2:72][C:73]([OH:75])=[O:74])[CH2:31]2)=[CH:47][CH:48]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131728209HCID 131728209, compound

Product 1

HCID 131728208HCID 131728208, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 3, Compound 6 (22 g, 23.2 mmol) was mixed with succinic anhydride (3.48 g, 34.8 mmol) and DMAP (0.283 g, 2.32 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (50 mL), triethylamine (7 g, 9.6 mL, 70 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 16 h. It was 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 was dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by column chromatography to afford compound 8 as white solid (21.7 g, 89% yield; Rf=0.5 in 10% MeOH/CHCl3).

Workup

  1. customdried in a vacuum at 40° C. overnight
  2. dissolutionThe mixture was dissolved in anhydrous dichloromethane (50 mL)
  3. washwashed with ice cold aqueous citric acid (5% wt., 100 mL) and water (2×100 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-337173eeef5e45bfb42594b6cc058b4e
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Reaction notes

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