Citric Acid → HCID 86632139, compound

HRID 253755Notes

Reaction equation

HRID 253755 reaction equation
[CH:1]([C@@H:5]([C:8](=[O:88])[NH:9][C@@H:10]([CH2:84][CH:85]([CH3:87])[CH3:86])[C:11](=[O:83])[N:12]([CH3:82])[C@@H:13]([CH2:78][CH:79]([CH3:81])[CH3:80])[C:14](=[O:77])[NH:15][C@@H:16]([CH3:76])[C:17](=[O:75])[NH:18][C@H:19]([CH3:74])[C:20](=[O:73])[N:21]([CH3:72])[C@@H:22]([CH2:68][CH:69]([CH3:71])[CH3:70])[C:23](=[O:67])[NH:24][C@@H:25]([CH2:63][CH:64]([CH3:66])[CH3:65])[C:26](=[O:62])[N:27]([CH3:61])[C@@H:28]([CH:58]([CH3:60])[CH3:59])[C:29](=[O:57])[N:30]([CH3:56])[C@@H:31]([C@H:48]([OH:55])[C@H:49]([CH3:54])[CH2:50]/[CH:51]=[CH:52]/[CH3:53])[C:32](=[O:47])[NH:33][C@@H:34]([C@H:44]([OH:46])[CH3:45])[C:35](=[O:43])[N:36]([CH3:42])[CH2:37][C:38]([O:40]C)=[O:39])[NH:6][CH3:7])([CH2:3][CH3:4])[CH3:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH:1]([C@@H:5]([C:8](=[O:88])[NH:9][C@@H:10]([CH2:84][CH:85]([CH3:87])[CH3:86])[C:11](=[O:83])[N:12]([CH3:82])[C@@H:13]([CH2:78][CH:79]([CH3:81])[CH3:80])[C:14](=[O:77])[NH:15][C@@H:16]([CH3:76])[C:17](=[O:75])[NH:18][C@H:19]([CH3:74])[C:20](=[O:73])[N:21]([CH3:72])[C@@H:22]([CH2:68][CH:69]([CH3:70])[CH3:71])[C:23](=[O:67])[NH:24][C@@H:25]([CH2:63][CH:64]([CH3:65])[CH3:66])[C:26](=[O:62])[N:27]([CH3:61])[C@@H:28]([CH:58]([CH3:59])[CH3:60])[C:29](=[O:57])[N:30]([CH3:56])[C@@H:31]([C@H:48]([OH:55])[C@H:49]([CH3:54])[CH2:50]/[CH:51]=[CH:52]/[CH3:53])[C:32](=[O:47])[NH:33][C@@H:34]([C@H:44]([OH:46])[CH3:45])[C:35](=[O:43])[N:36]([CH3:42])[CH2:37][C:38]([OH:40])=[O:39])[NH:6][CH3:7])([CH2:3][CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 86632140HCID 86632140, compound

Product 1

HCID 86632139HCID 86632139, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (3S,6S,9S,12S,15R,18S,21S,24S,27S,30S)-3-sec-butyl-30-[(1R)-1-hydroxyethyl]-27-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexen-1-yl]-6,9,18,21-tetraisobutyl-24-isopropyl-8,12,15,17,23,26,32-heptamethyl-4,7,10,13,16,19,22,25,28,31-decaoxo-2,5,8,11,14,17,20,23,26,29,32-undecaazatetratriacontan-34-oate (230 mg) in MeOH (4 ml) was added 1N LiOH (1.84 ml) under ice-bath cooling. After being stirred for 1 hr at the same temperature, the solution was acidified with 5% citric acid to be pH 5, concentrated in vacuo to remove MeOH, and extracted with AcOEt (20 ml). The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting residue was triturated with Et2O to give (3S,6S,9S,12S,15R,18S,21S,24S,27S,30S)-3-sec-butyl-30-[(1R)-1-hydroxyethyl]-27-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexen-1-yl]-6,9,18,21-tetraisobutyl-24-isopropyl-8,12,15,17,23,26,32-heptamethyl-4,7,10,13,16,19,22,25,28,31-decaoxo-2,5,8,11,14,17,20,23,26,29,32-undecaazatetratriacontan-34-oic acid (188 mg) as a solid.

Workup

  1. temperaturecooling
  2. concentrationconcentrated in vacuo
  3. customto remove MeOH
  4. extractionextracted with AcOEt (20 ml)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was triturated with Et2O

Sources & evidence

ORD record
ord-2441923dcc5d4e3aae316b4a87576178
Source dataset
uspto-grants-2011_01
Patent number
US07872097B2

Reaction notes

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