Pyridine, hydrofluoride (1:1) → HCID 12109153, compound

HRID 619269Notes

Reaction equation

HRID 619269 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[C@H:16]([NH:18][C:19](=[O:21])[CH3:20])[CH3:17])[C:9]([O:11][CH3:12])=[O:10].N1C=CC=CC=1.[FH:28]>>[C:19]([NH:18][C@@H:16]([C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[F:28])[CH3:17])(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 12109152HCID 12109152, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 12109153HCID 12109153, compound

Procedure

Sodium nitrite (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-eab272379dac491f82d86a31995aed39
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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