Boron trifluoride etherate → HCID 86737719, compound

HRID 2286333Notes

Reaction equation

HRID 2286333 reaction equation
[CH3:1][C@@:2]1([OH:18])[C@H:9]([CH3:10])[O:8][C@@H:5]([O:6][CH3:7])[CH2:4][C@@H:3]1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14].B(F)(F)F.[CH3:23]COCC.[N+](=C)=[N-]>C(Cl)Cl>[CH3:1][C@@:2]1([O:18][CH3:23])[C@H:9]([CH3:10])[O:8][C@@H:5]([O:6][CH3:7])[CH2:4][C@@H:3]1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:14])[F:15]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 9550DiazomethaneHCID 86737720HCID 86737720, compound

Product 1

HCID 86737719HCID 86737719, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 g (3.7 mmoles) of methyl 2,3,6-trideoxy-4-C-methyl-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (II-A) in 10 ml of dry methylene dichloride was treated at -70° with 0.05 ml of boron trifluoride etherate. While maintaining the temperature at -70°, an excess of diazomethane dissolved in methylene dichloride was added until a faint yellow color persisted. After 60 minutes at -70°, a white solid (polymethylene) was removed by filtration, and the filtrate was washed successively with 10% sodium bicarbonate solution and with water, after which it was dried with anhydrous magnesium sulfate. The residue which was obtained by evaporation was chromatographed on a silica-gel column. Elution with a 95:5 chloroform:acetone mixture gave pure methyl 2,3,6-trideoxy-4-C-methyl-4-O-methyl-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (II-B, 0.68 g, 65%) as a syrup; [α]D =-129° (c=1.1 in CHCl3); mass spectrum m/e 285 (M+). The pmr spectrum (CDCl3) showed absorptions at 1.22 (s, CH3 -C-4), 1.28 (d, CH3 -C-5), 3.33 and 3.48 (two s, --OCH3) and 4.77δ (broad s, C-1-H).

Workup

  1. temperatureWhile maintaining the temperature at -70°
  2. additionwas added until a faint yellow color
  3. customa white solid (polymethylene) was removed by filtration
  4. washthe filtrate was washed successively with 10% sodium bicarbonate solution and with water
  5. dry with materialafter which it was dried with anhydrous magnesium sulfate
  6. customThe residue which was obtained by evaporation
  7. customwas chromatographed on a silica-gel column
  8. washElution with a 95:5 chloroform

Sources & evidence

ORD record
ord-09db852619da4f27bd869ef13e5be9d4
Source dataset
uspto-grants-1981_05
Patent number
US04265885

Reaction notes

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