Trifluoroacetic anhydride → HCID 13477374, compound

HRID 868169Notes

Reaction equation

HRID 868169 reaction equation
[OH:1][C@:2]1([C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C:19](=[CH:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[C:11](=[CH2:25])[CH2:10]3)[CH2:7][C@@H:6]1[CH3:26])[C:3](=[O:5])[CH3:4].F[C:28](F)(F)[C:29](OC(=O)C(F)(F)F)=[O:30]>C(O)(=O)C>[C:29]([O:1][C@:2]1([C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C:19](=[CH:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[C:11](=[CH2:25])[CH2:10]3)[CH2:7][C@@H:6]1[CH3:26])[C:3](=[O:5])[CH3:4])(=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 13477372HCID 13477372, compound

Product 1

HCID 13477374HCID 13477374, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.3 g of 17α-hydroxy-16β-methyl-6-methylene-4,9(11)-pregnadiene-3,20-dione in 40 ml of glacial acetic acid is cooled to 0° C. and stirred, after adding 15 ml of trifluoroacetic acid anhydride dropwise, for one hour at room temperature. After precipitation into ice water-sodium chloride, the mixture is filtered off and worked up as usual. The crude product is purified on 450 g of silica gel with a hexane-ethyl acetate gradient (0-50% ethyl acetate), thus obtaining 2.3 g of 17α-acetoxy-16β-methyl-6-methylene-4,9(11)-pregnadiene-3,20-dione, mp 197°-198° C.

Workup

  1. customAfter precipitation into ice water-sodium chloride
  2. filtrationthe mixture is filtered off
  3. customThe crude product is purified on 450 g of silica gel with a hexane-ethyl acetate gradient (0-50% ethyl acetate)

Sources & evidence

ORD record
ord-afb609aada8d4b1badc3a312db548850
Source dataset
uspto-grants-1988_10
Patent number
US04777165

Reaction notes

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