Calcium Carbonate → HCID 86734029, compound

HRID 1576799Notes

Reaction equation

HRID 1576799 reaction equation
Br[C@H:2]1[C@H:22]([OH:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[C@H:3]1[CH2:4][CH2:5][C@@H:6]1[C@@H:18]2[C:17](=[O:25])[CH2:16][C@@:15]2([CH3:26])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C:11](=[O:14])[CH2:12][Br:13].C([O-])([O-])=O.[Ca+2].[Br-].[Li+]>CC(N(C)C)=O>[Br:13][CH2:12][C:11](=[O:14])[C@@H:10]1[C@:15]2([CH3:26])[C@H:7]([C@H:6]3[C@H:18]([C:17](=[O:25])[CH2:16]2)[C@:19]2([CH3:24])[C:3](=[CH:2][C@H:22]([OH:23])[CH2:21][CH2:20]2)[CH2:4][CH2:5]3)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 82050Lithium BromideHCID 86734034HCID 86734034, compound

Product 1

HCID 86734029HCID 86734029, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4β,21-Dibromo-3α-hydroxy-5α-pregnane-11,20-dione (200 mg.) in dry dimethyl acetamide (10 ml.) was treated with calofort U (1.5 g.) and lithium bromide (0.9 g.). The mixture was stirred at 85° for 31/2 hours. The reaction mixture was filtered, and the solid residue was washed with ether and ethyl acetate. The combined filtrate and washings were washed well (5 times) with water, dried over sodium sulphate and evaporated to a brown oil which was purified by preparative T.L.C. in ethyl acetate/petrol 1/1, the main band yielding title compound (70 mg.) as a colourless foam, [α]D + 140°.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid residue was washed with ether and ethyl acetate
  3. washThe combined filtrate and washings were washed well (5 times) with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated to a brown oil which
  6. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-5742b0f5ee8d42da88021a4689bb8b36
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

Loading…