Sulfuric Acid → 4-(7,12-Dihydroxy-3-methanesulfonyloxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl) pentanoic acid

HRID 1276105Notes

Reaction equation

HRID 1276105 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[S:30](Cl)([CH3:33])(=[O:32])=[O:31].OS(O)(=O)=O.CC(=O)OCC>N1C=CC=CC=1.O.C(O)(=O)C>[OH:27][CH:17]1[CH:16]2[CH:15]([CH2:14][CH:13]([OH:28])[C:12]3([CH3:29])[CH:11]2[CH2:10][CH2:9][CH:8]3[CH:2]([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:20]2([CH3:26])[CH:19]([CH2:24][CH:23]([O:25][S:30]([CH3:33])(=[O:32])=[O:31])[CH2:22][CH2:21]2)[CH2:18]1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 221493Cholic Acid

Product 1

HCID 184251314-(7,12-Dihydroxy-3-methanesulfonyloxy-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-17-yl) pentanoic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

100 g of cholic acid are dissolved in 500 ml of pyridine and 23.1 ml of mesyl chloride are added dropwise at 0° C. over a period of 30 minutes. The mixture is stirred at RT for 3 hours, then poured onto a solution of 400 ml of H2SO4 in 3 l of water at 0° C. and extracted 4 times with 750 ml of EA each time. The organic phase is dried over Na2SO4 and the solvent is removed in vacuo. The residue is crystallized using diisopropyl ether and 117.1 g are obtained; m.p. 121° C. (with decomposition). Rf (EA/HEP/acetic acid 5:5:1)=0.31 MS (FAB): 487 (M+H)+

Workup

  1. extractionextracted 4 times with 750 ml of EA each time
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customthe solvent is removed in vacuo
  4. customThe residue is crystallized
  5. customare obtained

Sources & evidence

ORD record
ord-4bb7fd5933aa45639c928c5bb31f2603
Source dataset
uspto-grants-2000_12
Patent number
US06166002

Reaction notes

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