Boron Trichloride → HCID 58370274, compound

HRID 2062117Notes

Reaction equation

HRID 2062117 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[F:20])[C:11]=1[O:21]COC)=[O:9])([CH3:6])[CH3:5].B(Cl)(Cl)Cl>ClCCl.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:25])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[F:20])[C:11]=1[OH:21])=[O:9])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 66701158HCID 66701158, compound

Product 1

HCID 58370274HCID 58370274, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-67.5 °C

Procedure

To a stirred solution of 0.107 g of 2-{[5-fluoro-1-(methoxymethoxyl)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 3 ml of dichloromethane at −65 to −70° C. was added by syringe 0.344 ml of 1M BCl3 in dichloromethane. The mixture was stirred for 10 minutes at −65 to −70° C. after which it was allowed to warm to RT and stirred at RT for 0.5 h. The mixture was poured into brine, extracted twice with ethyl acetate, dried, filtered and concentrated to an oil, which was chromatographed on silica gel eluting with ethyl acetate/dichloromethane/heptane to provide 0.088 g of 2-{[5-fluoro-1-(hydroxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester.

Workup

  1. temperatureto warm to RT
  2. stirringstirred at RT for 0.5 h
  3. extractionextracted twice with ethyl acetate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to an oil, which
  7. customwas chromatographed on silica gel eluting with ethyl acetate/dichloromethane/heptane

Sources & evidence

ORD record
ord-1f1ec5f01c1e411a8cd57c857bb41ee5
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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