Acetic Anhydride → HCID 86737612, compound

HRID 127858Notes

Reaction equation

HRID 127858 reaction equation
[F:1][C@:2]12[C@@H:24]([OH:25])[CH2:23][C@@:22]3([CH3:26])[C@@H:12]([CH2:13][C@@H:14]([OH:28])[C@:15]3([OH:27])[C:16](=[O:21])[C:17]([O:19][CH3:20])=[O:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:30])[CH:4]=[CH:5][C:6](=[O:29])[CH:7]=1.C(O[C:35](=[O:37])[CH3:36])(=O)C.[OH2:38].[C:39]1([CH3:49])C=CC(S(O)(=O)=O)=CC=1.[C:50]([O-])(=[O:52])[CH3:51].[Na+]>C(O)(=O)C>[C:50]([O:25][C@H:24]1[CH2:23][C@@:22]2([CH3:26])[C@@H:12]([CH2:13][C@@H:14]([O:28][C:35](=[O:37])[CH3:36])[C@:15]2([O:27][C:39](=[O:38])[CH3:49])[C:16](=[O:21])[C:17]([O:19][CH3:20])=[O:18])[C@H:11]2[C@@:2]1([F:1])[C@:3]1([CH3:30])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:29])[CH:5]=[CH:4]1)(=[O:52])[CH3:51]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86737611HCID 86737611, compound

Product 1

HCID 86737612HCID 86737612, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of (11β,16α)-9-fluoro-11,16,17-trihydroxy-3,20-dioxopregna-1,4-dien-21-oic acid, methyl ester (150 mg) in a mixture of glacial acetic acid (5.0 ml) and acetic anhydride (5.0 ml) containing p-toluene sulfonic acid hydrate (150 mg) is stirred for 40 hours. Sodium acetate (300 mg) is added and the solution is evaporated in vacuo. The residue is diluted with water, extracted with chloroform and the chloroform extract is washed with water, dried (MgSO4) and evaporated to a solid. The solid is crystallized from ethyl acetate to afford the title compound (164 mg), melting point 317°-319° C. (dec.) (discoloration starts from ca. 280° C.).

Workup

  1. customthe solution is evaporated in vacuo
  2. additionThe residue is diluted with water
  3. extractionextracted with chloroform
  4. extractionthe chloroform extract
  5. washis washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to a solid
  8. customThe solid is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-dd5435a8b671485c8ae4a61f25ec91b9
Source dataset
uspto-grants-1981_03
Patent number
US04257969

Reaction notes

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