Hydrochloric Acid → HCID 86738631, compound

HRID 2198786Notes

Reaction equation

HRID 2198786 reaction equation
O[C@@H:2]1[CH2:25][C@H:24]2[C@:19]([CH3:27])([CH2:20][CH2:21][C:22](=[O:26])[CH2:23]2)[C@@H:18]2[C@@H:3]1[C@H:4]1[C@:15]([CH3:29])([C:16](=[O:28])[CH2:17]2)[C@@H:7]([C@H:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.Cl>N1C=CC=CC=1>[O:26]=[C:22]1[CH2:21][CH2:20][C@@:19]2([CH3:27])[CH:24]([CH2:25][CH2:2][C@@H:3]3[C@@H:18]2[CH2:17][C:16](=[O:28])[C@@:15]2([CH3:29])[C@H:4]3[CH2:5][CH2:6][C@@H:7]2[C@H:8]([CH3:14])[CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH2:23]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 5283959HCID 5283959, compound

Product 1

HCID 86738631HCID 86738631, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a three-necked (round bottom) flask, 7α-hydroxy-3,12-diketo-5β-cholanic acid (3 g) obtained in the above examples was dissolved in pyridine (70 ml) and added thereto tosyl chloride (1 mol). The resulting mixture was reacted at 0° C. for 1 hour and then, refluxed for 5 hours. After reflux, 3 N aqueous hydrochloric acid was added and the reaction mixture was extracted with ether (100 ml). Ether was distilled off from the extract under a reduced pressure to give Δ6 - and/or Δ7 -3,12-diketo-cholenic acid (2.5 g). The resultant (2 g) was dissolved in 1 N aqueous sodium hydroxide (10 ml) and added thereto Raney nickel (0.1 g). After addition of hydrogen (0.01 mol), the mixture was reacted overnight to obtain 3α,12α-dihydroxy-5β-cholanic acid (deoxycholic acid) and 3α,12α-dihydroxy-5β-cholanic acid (yield: 90%).

Workup

  1. additionadded
  2. customThe resulting mixture was reacted at 0° C. for 1 hour
  3. temperaturerefluxed for 5 hours
  4. temperatureAfter reflux
  5. extractionthe reaction mixture was extracted with ether (100 ml)
  6. distillationEther was distilled off from the
  7. extractionextract under a reduced pressure

Sources & evidence

ORD record
ord-4520fc5575774043a1711deb040602f4
Source dataset
uspto-grants-1982_11
Patent number
US04359529

Reaction notes

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