Succinic anhydride → HCID 86584123, compound

HRID 1359619Notes

Reaction equation

HRID 1359619 reaction equation
[C:1]([O:20][CH2:21][C:22]([CH2:51][O:52][C:53](=[O:71])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]/[CH:61]=[CH:62]\[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])([CH2:30][O:31][C:32](=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[NH:23][CH2:24][CH2:25][S:26]([OH:29])(=[O:28])=[O:27])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.[C:79]1(=[O:85])[O:84][C:82](=[O:83])[CH2:81][CH2:80]1>C1COCC1>[C:1]([O:20][CH2:21][C:22]([CH2:30][O:31][C:32](=[O:50])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])([CH2:51][O:52][C:53](=[O:71])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]/[CH:61]=[CH:62]\[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH3:70])[N:23]([CH2:24][CH2:25][S:26]([OH:29])(=[O:28])=[O:27])[C:79](=[O:85])[CH2:80][CH2:81][C:82]([OH:84])=[O:83])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 9811924219315-98-7

Product 1

HCID 86584123HCID 86584123, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 566 mg (0.553 mmol) of 2-[tris(oleoyloxymethyl)methylamino]-1-ethanesulfonic acid in 10 mL THF was added 410 mg (4.06 mmol) of triethylamine. After 5 min 96 mg (0.960 mmol) of succinic anhydride was added. The yellow solution was stirred for 18 h under reflux. The solvent was removed under reduced pressure. The residual oil was purified by chromatography on silica gel, eluted with an ethyl acetate/methanol gradient (25:75 vol/vol to 0:100 vol/vol). N-[tris(oleoyloxymethyl)methyl]-N-(2-sulfoethyl)succinic acid monoamide was isolated as a yellow heavy viscous oil with a yield of 240 mg (38%).

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed under reduced pressure
  3. customThe residual oil was purified by chromatography on silica gel
  4. washeluted with an ethyl acetate/methanol gradient (25:75 vol/vol to 0:100 vol/vol)

Sources & evidence

ORD record
ord-7eb13336df54480d9b290c209070192a
Source dataset
uspto-grants-2003_07
Patent number
US06600059B2

Reaction notes

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