Succinic anhydride → HCID 131728232, compound

HRID 20933Notes

Reaction equation

HRID 20933 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[O:10][CH:11]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:12]2[CH2:16][CH:15]([OH:17])[CH2:14][N:13]2[C:18](=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([C:27]2[C:36](=[O:37])[C:35]3[C:30](=[N:31][C:32]([CH3:38])=[CH:33][CH:34]=3)[N:29]([CH2:39][CH3:40])[CH:28]=2)=[O:26])=[CH:5][CH:4]=1.[C:56]1(=[O:62])[O:61][C:59](=[O:60])[CH2:58][CH2:57]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:55][O:54][C:51]1[CH:50]=[CH:49][C:48]([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:10][CH:11]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:12]2[N:13]([C:18](=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([C:27]3[C:36](=[O:37])[C:35]4[C:30](=[N:31][C:32]([CH3:38])=[CH:33][CH:34]=4)[N:29]([CH2:39][CH3:40])[CH:28]=3)=[O:26])[CH2:14][CH:15]([O:17][C:56](=[O:62])[CH2:57][CH2:58][C:59]([OH:61])=[O:60])[CH2:16]2)=[CH:53][CH:52]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131728233HCID 131728233, compound

Product 1

HCID 131728232HCID 131728232, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 27, Compound 99 (1.48 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 (0.606 g, 0.96 mL, 6 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 μL). The organic phase is dried over anhydrous sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography to afford compound 101.

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 μL)
  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-55162a1c42bf433088601336a7b99ec7
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

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