Epichlorohydrin → HCID 53710830, compound

HRID 266023Notes

Reaction equation

HRID 266023 reaction equation
[OH-].[Na+].[CH2:3]([CH:5]1[O:7][CH2:6]1)Cl.[CH3:8][C:9]([O:12][C:13](=[O:40])[CH2:14][CH2:15][C@H:16]([C@@H:18]1[C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][C@@H:34]2[OH:37])[C@:30]2([CH3:31])[C@@H:25]([CH2:26][C@H:27]([OH:38])[CH2:28][CH2:29]2)[CH2:24][C@H:23]3[OH:39])[CH2:20][CH2:19]1)[CH3:17])([CH3:11])[CH3:10]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:8][C:9]([O:12][C:13](=[O:40])[CH2:14][CH2:15][C@H:16]([C@@H:18]1[C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][C@@H:34]2[OH:37])[C@:30]2([CH3:31])[C@@H:25]([CH2:26][C@H:27]([O:38][CH2:3][CH:5]4[O:7][CH2:6]4)[CH2:28][CH2:29]2)[CH2:24][C@H:23]3[OH:39])[CH2:20][CH2:19]1)[CH3:17])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 11016067HCID 11016067, compound

Product 1

HCID 53710830HCID 53710830, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 50% NaOH (10 ml), epichlorohydrin (6 ml) and tetrabutylammonium hydrogen sulfate (0.3 g) kept at 0° C. was added drop by drop to a solution of (3α,5β,7α,12α)-3,7,12-trihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester (prepared according to the procedure described by R. P. Bonar-Law et al., J. Chem. Soc. Perkin Trans. I, 1990, 2245) (0.0045 mol) in CH2Cl2 (10 ml). When the addition was completed the mixture was left to react at room temperature by 24 h. The organic phase was separated, washed with H2O to neutral, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography to obtain 0.86 g of desired product (0.0017 mol).

Workup

  1. customkept at 0° C.
  2. customprepared
  3. additionWhen the addition
  4. waitwas left
  5. customto react at room temperature by 24 h
  6. customThe organic phase was separated
  7. washwashed with H2O to neutral,
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b83fdc54deb641d099b352f681b66431
Source dataset
uspto-grants-1997_07
Patent number
US05649537

Reaction notes

Loading…