Succinic anhydride → HCID 131728210, compound

HRID 2402995Notes

Reaction equation

HRID 2402995 reaction equation
[CH2:1]([O:19][CH:20]([CH2:64][O:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])[CH2:21][O:22][C:23](=[O:63])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]1[CH2:36][CH:35]([OH:37])[CH2:34][CH:33]1[CH:38]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[O:39][CH:40]([C:49]1[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=1)[C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:84]1(=[O:90])[O:89][C:87](=[O:88])[CH2:86][CH2:85]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([CH:40]([C:49]2[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=2)[O:39][CH:38]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:33]2[N:32]([C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:23]([O:22][CH2:21][CH:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:64][O:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH3:83])=[O:63])[CH2:36][CH:35]([O:37][C:84](=[O:90])[CH2:85][CH2:86][C:87]([OH:89])=[O:88])[CH2:34]2)=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131728211HCID 131728211, compound

Product 1

HCID 131728210HCID 131728210, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 5, Compound 12 (5.6 g, 4.8 mmol) was mixed with succinic anhydride (0.727 g, 7.26 mmol) and DMAP (0.062 g, 0.5 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (20 mL), triethylamine (1.52 g, 2 mL, 15 mmol) was added and the solution was stirred at room temperature under argon atmosphere for 16 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 to afford compound 14 as white solid (2.85 g, 47% yield; Rf=0.65 in 10% MeOH/CHCl3).

Workup

  1. customdried in a vacuum at 40° C. overnight
  2. dissolutionThe mixture was dissolved in anhydrous dichloromethane (20 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-5d9f576de10e475cb7a90c61ef53e9e1
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Reaction notes

Loading…