Acetic Anhydride → HCID 21478721, compound

HRID 2292492Notes

Reaction equation

HRID 2292492 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:22])=[C:13]([CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O-:26])(=O)[CH3:24].[K+].C(OC(=O)C)(=O)C.[N:35](OCCC(C)C)=O>C1C=CC=CC=1>[C:23]([N:22]1[C:12]2[C:13](=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[C:15]([C:16]([O:18][CH:19]([CH3:20])[CH3:21])=[O:17])=[N:35]1)(=[O:26])[CH3:24]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 21478799HCID 21478799, compound

Product 1

HCID 21478721HCID 21478721, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of isopropyl 5-benzyloxy-2-aminophenylactate (13.2 g) in benzene (140 ml) were added potassium acetate (4.33 g) and then acetic anhydride (13.5 g) and the mixture was heated under reflux for 20 minutes. A solution of isopentyl nitrite (7.76 g) in benzene (30 ml) was added dropwise over 5 minutes under reflux and then refluxing was continued for further 3 hours. After allowing to cool to room temperature, insolubles were filtered off with Celite and concentrated under reduced pressure. The resulting residue (16.9 g) was purified by a silica gel column chromatography (hexane:ethyl acetate=9:1-4:1) to give the title compound (10.9 g).

Workup

  1. temperatureunder reflux for 20 minutes
  2. temperatureunder reflux
  3. temperaturerefluxing
  4. filtrationinsolubles were filtered off with Celite
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue (16.9 g) was purified by a silica gel column chromatography (hexane:ethyl acetate=9:1-4:1)

Sources & evidence

ORD record
ord-0c4788772b7245fb9a6581769e132543
Source dataset
uspto-grants-1997_11
Patent number
US05684003

Reaction notes

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