Succinic anhydride → HCID 131728210, compound

HRID 1055776Notes

Reaction equation

HRID 1055776 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 131728211(6-[2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl]-6-oxo-hexyl)-carbamic acid 2,3-bis-octadecyloxy-propyl Ester

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-f7b4df35efc347dd98f764f85f57ad86
Source dataset
uspto-grants-2016_07
Patent number
US09394540B2

Reaction notes

Loading…