Acetic Anhydride → HCID 86736014, compound

HRID 1763853Notes

Reaction equation

HRID 1763853 reaction equation
[Cl:1][CH2:2][C:3](=[O:26])[C:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@:18]([F:24])([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:25])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH:5]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:27]([O:23][C@H:19]1[CH2:20][C@@:21]2([CH3:22])[C@@H:7]([CH2:6][CH:5]=[C:4]2[C:3](=[O:26])[CH2:2][Cl:1])[C@H:8]2[C@@:18]1([F:24])[C@:16]1([CH3:17])[C:11]([CH2:10][CH2:9]2)=[CH:12][C:13](=[O:25])[CH:14]=[CH:15]1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 23681166Acetic acid, sodium salt, monohydrateHCID 86736012HCID 86736012, compound

Product 1

HCID 86736014HCID 86736014, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 21-chloro-9-fluoro-11β-hydroxypregna-1,4,16-triene-3,20-dione (2.1g) in a mixture of glacial acetic acid (30 ml) and acetic anhydride (30 ml) containing p-toluenesulfonic acid hydrate (2.1g) is stirred at room temperature. After 30 hours the solution is mixed with sodium acetate hydrate (5.0g) and evaporated in vacuo. The residue is dissolved in chloroform, washed with water, dried and evaporated to afford the title compound. One crystallization from acetone affords 1.85g of the title compound, melting point 222°-223° C. (dec).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue is dissolved in chloroform
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-9968b40f8d9943f9b02026a28c0626e1
Source dataset
uspto-grants-1978_09
Patent number
US04113722

Reaction notes

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