Succinic anhydride → HCID 131728227, compound

HRID 1893052Notes

Reaction equation

HRID 1893052 reaction equation
[CH2:1]([N:19]([CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH3:104])[C:20]([CH2:22][CH2:23][CH:24]([CH:26]1[C:42]2([CH3:43])[CH:29]([CH:30]3[CH:39]([CH2:40][CH2:41]2)[C:38]2([CH3:44])[CH:33]([CH2:34][CH:35]([O:45][C:46](=[O:86])[NH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([N:55]4[CH2:59][CH:58]([OH:60])[CH2:57][CH:56]4[CH:61]([C:80]4[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=4)[O:62][CH:63]([C:72]4[CH:77]=[CH:76][C:75]([O:78][CH3:79])=[CH:74][CH:73]=4)[C:64]4[CH:69]=[CH:68][C:67]([O:70][CH3:71])=[CH:66][CH:65]=4)=[O:54])[CH2:36][CH2:37]2)[CH2:32][CH2:31]3)[CH2:28][CH2:27]1)[CH3:25])=[O:21])[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:105]1(=[O:111])[O:110][C:108](=[O:109])[CH2:107][CH2:106]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:71][O:70][C:67]1[CH:68]=[CH:69][C:64]([CH:63]([C:72]2[CH:77]=[CH:76][C:75]([O:78][CH3:79])=[CH:74][CH:73]=2)[O:62][CH:61]([C:80]2[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=2)[CH:56]2[N:55]([C:53](=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][NH:47][C:46]([O:45][CH:35]3[CH2:34][CH:33]4[C:38]([CH3:44])([CH:39]5[CH:30]([CH2:31][CH2:32]4)[CH:29]4[C:42]([CH3:43])([CH:26]([CH:24]([CH3:25])[CH2:23][CH2:22][C:20](=[O:21])[N: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])[CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH3:104])[CH2:27][CH2:28]4)[CH2:41][CH2:40]5)[CH2:37][CH2:36]3)=[O:86])[CH2:59][CH:58]([O:60][C:105](=[O:111])[CH2:106][CH2:107][C:108]([OH:110])=[O:109])[CH2:57]2)=[CH:65][CH:66]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131728228HCID 131728228, compound

Product 1

HCID 131728227HCID 131728227, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 21, Compound 84 (1.44 g, 1 mmol) was mixed with succinic anhydride (0.15 g, 1.5 mmol) and DMAP (0.0122 g, 01 mmol) and dried in a vacuum at 40° C. overnight. The mixture was dissolved in anhydrous dichloromethane (5 mL), triethylamine (0.101 g, 0.14 mL, 1 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., 25 mL) and water (2×25 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 86 as white solid (1.1 g, 71% 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 (5 mL)
  3. washwashed with ice cold aqueous citric acid (5% wt., 25 mL) and water (2×25 mL) The organic phase
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-3596a67e5eac456f865d684a18561782
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Reaction notes

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