Acetic Acid → 2-(5-(L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane

HRID 489090Notes

Reaction equation

HRID 489090 reaction equation
C([NH:20][C@H:21]([C:25]([O:27][CH2:28][CH:29]([CH2:69][O:70][C:71](=[O:89])[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH2:53][O:54][C:55]1[CH:64]=[CH:63][CH:62]=[C:61]2[C:56]=1[C:57](=[O:68])[CH:58]=[C:59]([C:65]([OH:67])=[O:66])[O:60]2)[CH2:37][O:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[C:41](=[O:52])[CH:42]=[C:43]([C:49]([OH:51])=[O:50])[O:44]2)=[O:34])=[O:26])[CH:22]([CH3:24])[CH3:23])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C>C(OCC)(=O)C>[NH2:20][C@H:21]([C:25]([O:27][CH2:28][CH:29]([CH2:69][O:70][C:71](=[O:89])[CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH2:37][O:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[C:41](=[O:52])[CH:42]=[C:43]([C:49]([OH:51])=[O:50])[O:44]2)[CH2:53][O:54][C:55]1[CH:64]=[CH:63][CH:62]=[C:61]2[C:56]=1[C:57](=[O:68])[CH:58]=[C:59]([C:65]([OH:67])=[O:66])[O:60]2)=[O:34])=[O:26])[CH:22]([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 233875142-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane

Product 1

HCID 545218722-(5-(L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dibenzyl ester of 2-[5-(N-trityl-L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane (238 mg, (0.17 mmol) was dissolved in ethyl acetate (1.5 ml). To the solution was added 80% acetic acid (10 ml). After two hr, the solution was evaporated and purified by column chromatography to yield 197 mg of 2-(5-(L-valyloxymethyl)-6-stearoyloxyhexanoyloxy]-1,3-bis-(2-carboxychromon-5-yloxy)propane.

Workup

  1. customthe solution was evaporated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-3d48e1fa954445bfb5eaee12e06ffe40
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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