Acetic Anhydride → HCID 14834656, compound

HRID 1722288Notes

Reaction equation

HRID 1722288 reaction equation
[F:1][C:2]1[C:3]([N:14]2[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15]2)=[C:4]([C:7]([F:13])=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH2:5][OH:6].[C:20](OC(=O)C)(=[O:22])[CH3:21]>O>[C:20]([NH:19][CH:16]1[CH2:17][CH2:18][N:14]([C:3]2[C:2]([F:1])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[C:7]([F:13])[C:4]=2[CH2:5][OH:6])[CH2:15]1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14834655HCID 14834655, compound

Product 1

HCID 14834656HCID 14834656, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3,6-difluoro-2-(3-amino-1-pyrrolidinyl)-5-nitrobenzyl alcohol (43 mg) is added acetic anhydride (0.5 ml) at room temperature. The mixture is stirred at the same temperature for 10 minutes, and the reaction mixture is diluted with water and extracted with dichloromethane. The organic layer is washed with water and aqueous saturated sodium chloride in this order and dried over anhydrous magnesium sulfate, and then solvent is distilled off. The resulting residue is purified by silica gel column chromatography (solvent, dichloromethane→methanol:dichloromethane=1:12) and then recrystallized from dichloromethane to give 2-(3-acetylamino-1-pyrrolidinyl)-3,6-difluoro-5-nitrobenzyl alcohol (40 mg), as yellow prisms, m.p. 142.5°-143.5° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer is washed with water and aqueous saturated sodium chloride in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationsolvent is distilled off
  5. customThe resulting residue is purified by silica gel column chromatography (solvent, dichloromethane→methanol:dichloromethane=1:12)
  6. customrecrystallized from dichloromethane

Sources & evidence

ORD record
ord-20806e8231fc4dd39d844d9ec423fed3
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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