Water → HCID 131724325, compound

HRID 270248Notes

Reaction equation

HRID 270248 reaction equation
[OH-:1].[K+].CO.O.[CH3:6][C@@H:7]([C@@H:14]1[C@@:18]2([CH3:35])[CH2:19][CH2:20][C:21]3[C@@:26]4([CH3:34])[CH2:27][CH2:28][C@H:29]([OH:33])[C:30]([CH3:32])([CH3:31])[C@@H:25]4[CH2:24][CH2:23][C:22]=3[C@:17]2([CH3:36])[CH2:16][CH2:15]1)[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12]>CCCCCC.CCOCC>[CH3:13][C:11]([CH3:12])=[CH:10][CH2:9][CH2:8]/[C:7](/[CH3:6])=[CH:14]/[CH2:15][CH2:12]/[C:11](/[CH3:13])=[CH:10]/[CH2:9][CH2:8]/[CH:7]=[C:14](/[CH2:18][CH2:35]/[CH:16]=[C:17](/[CH2:18][CH2:19][CH:20]1[O:1][C:21]1([CH3:22])[CH3:26])\[CH3:36])\[CH3:15].[CH3:6][C@@H:7]([C@@H:14]1[C@@:18]2([CH3:35])[CH2:19][CH2:20][C:21]3[C@@:26]4([CH3:34])[CH2:27][CH2:28][C@H:29]([OH:33])[C:30]([CH3:32])([CH3:31])[C@@H:25]4[CH2:24][CH2:23][C:22]=3[C@:17]2([CH3:36])[CH2:16][CH2:15]1)[CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 246983LanosterolHCID 23689386Potassium hydroxide methanol

Product 1

HCID 131724325HCID 131724325, compound

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent2×

Procedure

After 1 hour at 37° C. the reaction was stopped by the addition of 0.6 ml of 10% KOH-methanol, 0.7 ml of water and 0.1 ml of hexane:ether (1:1, v/v) which contained 25 μg of non-radioactive MOS and 25 μg of lanosterol as carriers. After shaking, 1 ml of hexane:ether (1:1, v/v) was added to each test tube, these were again shaken and then centrifuged. The upper phase was transferred into a glass test tube, the lower phase was again extracted with hexane:ether and combined with the first extract. The entire extract was evaporated to dryness with nitrogen, the residue was suspended in 50 μl of hexane:ether and applied to a silica gel plate. Chromatographic separation was effected in hexane:ether (1:1, v/v) as the eluent. The Rf values for the MOS substrate and the lanosterol product were 0.91 and, respectively, 0.54. After drying, radioactive MOS and lanosterol were observed on the silica gel plate. The ratio of MOS to lanosterol was determined from the radioactive bands in order to determine the yield of the reaction and OSC inhibition.

Workup

  1. stirringthese were again shaken
  2. customThe upper phase was transferred into a glass test tube
  3. extractionthe lower phase was again extracted with hexane
  4. extractionThe entire extract
  5. customwas evaporated to dryness with nitrogen
  6. customChromatographic separation
  7. customAfter drying
  8. customthe yield of the reaction and OSC inhibition

Sources & evidence

ORD record
ord-fa130f893a434f3890bd8690ad2aebe7
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

Loading…