Succinic anhydride → Succinic Acid mono-(5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-{6-[2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethoxycarbonylamino]-hexanoyl}-pyrrolidin-3-yl)ester

HRID 1893022Notes

Reaction equation

HRID 1893022 reaction equation
[CH2:1]([C:17]1([CH3:75])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([CH3:74])[C:21]([CH3:73])=[C:22]([O:28][CH2:29][CH2:30][O:31][C:32](=[O:72])[NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([N:41]3[CH2:45][CH:44]([OH:46])[CH2:43][CH:42]3[CH:47]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[O:48][CH:49]([C:58]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=3)[C:50]3[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=3)=[O:40])[C:23]=2[CH3:27])[O:18]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][CH3:16].[C:76]1(=[O:82])[O:81][C:79](=[O:80])[CH2:78][CH2:77]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:57][O:56][C:53]1[CH:54]=[CH:55][C:50]([CH:49]([C:58]2[CH:59]=[CH:60][C:61]([O:64][CH3:65])=[CH:62][CH:63]=2)[O:48][CH:47]([C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:42]2[N:41]([C:39](=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][NH:33][C:32]([O:31][CH2:30][CH2:29][O:28][C:22]3[C:23]([CH3:27])=[C:24]4[C:19](=[C:20]([CH3:74])[C:21]=3[CH3:73])[O:18][C:17]([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][CH3:16])([CH3:75])[CH2:26][CH2:25]4)=[O:72])[CH2:45][CH:44]([O:46][C:76](=[O:82])[CH2:77][CH2:78][C:79]([OH:81])=[O:80])[CH2:43]2)=[CH:51][CH:52]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 131728212(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic acid 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl Ester

Product 1

HCID 131728213Succinic Acid mono-(5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-{6-[2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethoxycarbonylamino]-hexanoyl}-pyrrolidin-3-yl)esterYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Referring to scheme 7, Compound 19 (5.1 g, 5 mmol) was mixed with succinic anhydride (0.75 g, 7.5 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 (25 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 21 as white foamy solid (2.85 g, 51% 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 (25 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-51f911cf9ac84c9fa98075cf9af8f870
Source dataset
uspto-grants-2013_08
Patent number
US08507661B2

Reaction notes

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