Citric Acid → HCID 86632139, compound

HRID 889626Notes

Reaction equation

HRID 889626 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-e594248f11aa4e86932d23de0242e68f
Source dataset
uspto-grants-2012_08
Patent number
US08252895B2

Reaction notes

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