Succinic anhydride → HCID 131728226, compound

HRID 20925Notes

Reaction equation

HRID 20925 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)[O:10][CH:11]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:12]2[CH:16]([OH:17])[CH2:15][N:14]([C:18](=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:32](=[O:33])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]3=[O:34])[CH2:13]2)=[CH:5][CH:4]=1.[C:50]1(=[O:56])[O:55][C:53](=[O:54])[CH2:52][CH2:51]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:49][O:48][C:45]1[CH:46]=[CH:47][C:42]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[O:10][CH:11]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:12]2[CH2:13][N:14]([C:18](=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]3[C:32](=[O:33])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]3=[O:34])[CH2:15][CH:16]2[O:17][C:50](=[O:56])[CH2:51][CH2:52][C:53]([OH:55])=[O:54])=[CH:43][CH:44]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 1317282252-(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

Product 1

HCID 131728226HCID 131728226, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 19, Compound 77 (2 g, 3 mmol) was mixed with succinic anhydride (0.600 g, 6 mmol) and DMAP (0.366 g, 3 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (5 mL), triethylamine (0.913 g, 1.25 mL, 9 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 4 h. It was then diluted with dichloromethane (50 mL) and washed with ice cold aqueous citric acid (5% wt., 50 mL) and water (2×50 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by column chromatography using 6% MeOH/DCM to afford compound 79 as white solid (2.05 g, 89% yield; Rf=0.4 in 10% MeOH/CHCl3).

Workup

  1. customdried in a vacuum at 40° C. overnight
  2. dissolutionThe mixture was dissolved in anhydrous dichloromethane (5 mL)
  3. washwashed with ice cold aqueous citric acid (5% wt., 50 mL) and water (2×50 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-ca0e9d69e55f4ca4aca9ca62e16ebb73
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

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