Sodium Nitrate → HCID 12109153, compound

HRID 1274186Notes

Reaction equation

HRID 1274186 reaction equation
[N+]([O-])([O-])=O.[Na+].N[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[C@H:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[C:10]([O:12][CH3:13])=[O:11].N1C=CC=CC=1.[FH:29]>>[C:20]([NH:19][C@@H:17]([C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[F:29])[CH3:18])(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 24268Sodium NitrateHCID 64774Pyridine, hydrofluoride (1:1)HCID 12109152HCID 12109152, compound

Product 1

HCID 12109153HCID 12109153, compound

Procedure

Sodium nitrate (640 mg) was added to a solution of methyl (R)-3-amino-4-(1-acetamidoethyl)benzoate (2 g) in hydrogen fluoride-pyridine (20 ml) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After the reaction, the reaction mixture was poured into ice water and extracted with chloroform. The extract was washed with water, dried and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to give 690 mg of methyl (R)-4-(1-acetamidoethyl)-3-fluorobenzoate.

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-ff7c346a414e4c609f15b09f2e7fd1a9
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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