Triethylamine → HCID 86743809, compound

HRID 1165454Notes

Reaction equation

HRID 1165454 reaction equation
[SH:1][CH2:2][C@@:3]12[C@@H:22]3[C@H:11]([C@H:12]4[C@:19]([CH3:23])([CH2:20][CH2:21]3)[C@@H:15]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:24])[CH2:5][CH2:4]2.[F:25][C:26]([F:37])([F:36])[C:27]([O:29]C(=O)C(F)(F)F)=[O:28].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[F:25][C:26]([F:37])([F:36])[C:27]([OH:29])=[O:28].[SH:1][CH2:2][C@@:3]12[C@@H:22]3[C@H:11]([C@H:12]4[C@:19]([CH3:23])([CH2:20][CH2:21]3)[C@@H:15]([C:16](=[O:18])[CH3:17])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:24])[CH2:5][CH2:4]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14695953HCID 14695953, compound

Product 1

HCID 86743809HCID 86743809, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.47 g of 19-mercaptopregn-4-ene-3,20-dione and 4-dimethylaminopyridine in 50 ml of dichloromethane is chilled to 0° C. and treated with 4.2 ml of trifluoroacetic anhydride and 8.4 ml of triethylamine. The ice-bath is removed and the solution allowed to stir for 1 hour. The solution is concentrated. The residue is taken up in ether and washed once with 1N hydrochloric acid, twice with water and once with sodium bicarbonate solution and brine. The resulting solution is dried and concentrated. Recrystallization of the resulting residue from ethyl acetate/hexane provides 19-mercaptopregn-4-ene-3,20-dione trifluoroacetate as white crystals.

Workup

  1. customThe ice-bath is removed
  2. concentrationThe solution is concentrated
  3. washwashed once with 1N hydrochloric acid, twice with water and once with sodium bicarbonate solution and brine
  4. customThe resulting solution is dried
  5. concentrationconcentrated
  6. customRecrystallization of the resulting residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c78a089aac3a4dca8b20ae7dcee7d56a
Source dataset
uspto-grants-1990_03
Patent number
US04910191

Reaction notes

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