Dimethyl Sulfoxide → HCID 117736061, compound

HRID 1482225Notes

Reaction equation

HRID 1482225 reaction equation
[CH2:1]([C@H:8]1[C:37](=[O:38])[N:36]([CH3:39])[C@@H:35]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:34](=[O:44])[NH:33][C@@H:32]([C@H:45]([OH:47])[CH3:46])[C:31](=[O:48])[N:30]([CH3:49])[CH2:29][C:28](=[O:50])[N:27]([CH3:51])[C@@H:26]([CH2:52][CH:53]([CH3:55])[CH3:54])[C:25](=[O:56])[NH:24][C@@H:23]([CH2:57][O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[C:22](=[O:63])[N:21]([CH3:64])[C@@H:20]([C@H:65]([CH2:67][CH3:68])[CH3:66])[C:19](=[O:69])[NH:18][C@H:17]([C:70]([N:72]2[CH2:77][CH2:76][CH2:75][CH2:74][CH2:73]2)=[O:71])[CH2:16][S:15][CH2:14][C:13](=[O:78])[N:12]([CH3:79])[C@@H:11]([CH3:80])[C:10](=[O:81])[N:9]1[CH3:82])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH:84]OS([O-])=O.[K+].CS(C)=O>CO>[CH2:1]([C@H:8]1[C:37](=[O:38])[N:36]([CH3:39])[C@@H:35]([CH2:40][CH:41]([CH3:42])[CH3:43])[C:34](=[O:44])[NH:33][C@@H:32]([C@H:45]([OH:47])[CH3:46])[C:31](=[O:48])[N:30]([CH3:49])[CH2:29][C:28](=[O:50])[N:27]([CH3:51])[C@@H:26]([CH2:52][CH:53]([CH3:55])[CH3:54])[C:25](=[O:56])[NH:24][C@@H:23]([CH2:57][O:58][C:59]([CH3:60])([CH3:62])[CH3:61])[C:22](=[O:63])[N:21]([CH3:64])[C@@H:20]([C@H:65]([CH2:67][CH3:68])[CH3:66])[C:19](=[O:69])[NH:18][C@H:17]([C:70]([N:72]2[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77]2)=[O:71])[CH2:16][S:15](=[O:84])[CH2:14][C:13](=[O:78])[N:12]([CH3:79])[C@@H:11]([CH3:80])[C:10](=[O:81])[N:9]1[CH3:82])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 117736057HCID 117736057, compound2×

Product 1

HCID 117736061HCID 117736061, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5S,8S,11S,14S,20S,23S,26S,29R)-8-Benzyl-23-(tert-butoxymethyl)-26-((S)-sec-butyl)-14-((R)-1-hydroxyethyl)-11,20-diisobutyl-4,5,7,10,16,19,25-heptamethyl-29-(piperidine-1-carbonyl)-1-thia-4,7,10,13,16,19,22,25,28-nonaazacyclotriacontane-3,6,9,12,15,18,21,24,27-nonone (Compound P-109) (9.5 mg, 8.11×10−3 mmol) was dissolved in methanol (0.5 ml), and water (0.25 ml) was added. The solution was cooled in an ice bath with stirring, and oxone (5.5 mg, 8.92×10−3 mmol) was added. The reaction mixture was stirred under ice-cooling for 25 minutes, and DMSO (80 μl) was then added. The mixture was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=60/40→0/100) to afford (5S,8S,11S,14S,20S,23S,26S,29R)-8-benzyl-23-(tert-butoxymethyl)-26-((S)-sec-butyl)-14-((R)-1-hydroxyethyl)-11,20-diisobutyl-4,5,7,10,16,19,25-heptamethyl-29-(piperidine-1-carbonyl)-1-thia-4,7,10,13,16,19,22,25,28-nonaazacyclotriacontane-3,6,9,12,15,18,21,24,27-nonone 1-oxide (Compound P-114) (8.6 mg, 90%).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. stirringThe reaction mixture was stirred under ice-
  3. temperaturecooling for 25 minutes
  4. customThe mixture was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=60/40→0/100)

Sources & evidence

ORD record
ord-650f1fc8f67f44cfb426cff36dfc2c07
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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