Boron trifluoride etherate → HCID 86736777, compound

HRID 2052236Notes

Reaction equation

HRID 2052236 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C@@H:6]1[C@H:13]([OH:14])[C@H:12]([CH3:15])[O:11][C@@H:8]([O:9][CH3:10])[CH2:7]1)=[O:4].B(F)(F)F.[CH3:22]COCC.[N+](=C)=[N-]>C(Cl)Cl>[F:17][C:2]([F:1])([F:16])[C:3]([NH:5][C@@H:6]1[C@H:13]([O:14][CH3:22])[C@H:12]([CH3:15])[O:11][C@@H:8]([O:9][CH3:10])[CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 9550DiazomethaneHCID 12836815HCID 12836815, compound

Product 1

HCID 86736777HCID 86736777, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.57 g.; 10 mmoles of methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (II-A) in 45 ml. of dry methylene dichloride was treated at 0° C. with 0.1 ml. of boron trifluoride etherate. While maintaining the temperature at 0°, an excess of diazomethane dissolved in methylene dichloride was added until a faint yellow color persisted. After 90 minutes at 0°, 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 crystallized from ethyl ether-hexane to give pure methyl 2,3,6-trideoxy-3-trifluoroacetamido-4-O-methyl-α-L-lyxo-hexopyranoside (II-B, 2.3 g., 85%): m.p. 137°-138°; [α]D =-150° (c=1, in CHCl3); mass spectrum m/e 271 (M+). The pmr spectrum (CDCl3) showed absorptions at 1.23 (d, CH3 --C-- 5), 3.23 and 3.40 (two s, --OCH3) and 4.70δ (broad s, C--1--H).

Workup

  1. temperatureWhile maintaining the temperature at 0°
  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 crystallized from ethyl ether-hexane

Sources & evidence

ORD record
ord-9ad108207f1f4df4a773e95669b7cb73
Source dataset
uspto-grants-1980_01
Patent number
US04183919

Reaction notes

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