Boron trifluoride etherate → HCID 86737818, compound

HRID 1680808Notes

Reaction equation

HRID 1680808 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>[CH3:22][O:14][C@H:13]1[C@H:12]([CH3:15])[O:11][C@@H:8]([O:9][CH3:10])[CH2:7][C@H:6]1[NH:5][C:3](=[O:4])[C:2]([F:1])([F:16])[F:17]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 9550DiazomethaneHCID 12836807HCID 12836807, compound

Product 1

HCID 86737818HCID 86737818, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of 11.7 g; 45 mmol of methyl 2,3,6-trideoxy-3-trifluroacetamido-α-L-ribohexopyranoside (V) in 100 ml of anhydrous methylene dichloride was treated at -70° C. with 0.6 ml of boron trifluoride etherate. While maintaining the temperature at -70° C., an excess of diazomethane in anhydrous methylene dichloride was added until a faint yellow color persisted. After 60 minutes at -70° C., a white solid (polymethylene) which precipitated out, was removed by filtration. The filtrate was washed successively with a 10% sodium bicarbonate solution and water, and then dried over anhydrous sodium sulphate. The filtrate was then evaporated to leave a residue, which was then chromatographed on a silica gel column. Elution of the column with chloroform gave pure methyl 4-O-methyl-2,3,6-trideoxy-3-trifluoroacetamido-α-L-ribohexopyranoside (VI) as an amorphous solid; m.p. 55°-60° C; [α]D23° =-110° (c=0.5 in CHCl3); mass spectrum: m/e 271 (M+). The p.m.r. spectrum showed absorption at: 1.30 (d, CH3 --C--5), 2.95 (dd, J=9.5 and 4.0 Hz, C--4--H), 3.42 and 3.43 (s,2 CH3O--), 3.70 (dq, J=6.0 and 9.0 Hz, C--5--H), 4.45-4.85 (m, C--3--H) and 4.75 δ (broad s WH =5.5 Hz, C--1--H).

Workup

  1. customa white solid (polymethylene) which precipitated out
  2. customwas removed by filtration
  3. washThe filtrate was washed successively with a 10% sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe filtrate was then evaporated
  6. customto leave a residue, which
  7. customwas then chromatographed on a silica gel column
  8. washElution of the column with chloroform

Sources & evidence

ORD record
ord-3aa514ba6fe1452296147a714e47e70c
Source dataset
uspto-grants-1981_06
Patent number
US04276289

Reaction notes

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