Boron tribromide → (2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-hydroxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

HRID 46220Notes

Reaction equation

HRID 46220 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][C:9]([CH2:11][C:12]2[CH:13]=[C:14]([C@H:24]3[C@H:29]([OH:30])[C@@H:28]([OH:31])[C@H:27]([OH:32])[C@@H:26]([CH2:33][OH:34])[O:25]3)[C:15]3[C:20]([C:21]=2[O:22]C)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:8][N:7]=1.B(Br)(Br)Br>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][C:9]([CH2:11][C:12]2[CH:13]=[C:14]([C@H:24]3[C@H:29]([OH:30])[C@@H:28]([OH:31])[C@H:27]([OH:32])[C@@H:26]([CH2:33][OH:34])[O:25]3)[C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 49846153HCID 49846153, compound2×

Product 1

HCID 49846230(2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-hydroxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triolYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-methoxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (compound 71b, 50 mg, 0.10 mmol) in CH2Cl2 (5 mL) at 0° C. was added boron tribromide (1.0 M in CH2Cl2, 0.52 mL, 0.52 mmol). The resulting mixture was stirred with gradual warming to ambient temperature over 2 h and re-cooled to 0° C. The mixture was quenched with MeOH and concentrated in vacuo. The resulting crude residue was purified by reverse phase preparative HPLC to yield the title compound (36 mg, 74%) as a white solid.

Workup

  1. temperaturere-cooled to 0° C
  2. customThe mixture was quenched with MeOH
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-1f8d2c095c3f4a249910d0935901553b
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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