Acetonitrile → HCID 25169378, compound

HRID 1175331Notes

Reaction equation

HRID 1175331 reaction equation
[CH2:1]([O:5][CH2:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=2)=[CH:9][C:8]=1[C:23]1(OC)[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@H:26]([OH:31])[C@@H:25]([CH2:32][OH:33])[O:24]1)[CH2:2][C:3]#[CH:4].CC#N.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:5][CH2:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH3:22])=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C@H:23]1[C@H:28]([OH:29])[C@@H:27]([OH:30])[C@H:26]([OH:31])[C@@H:25]([CH2:32][OH:33])[O:24]1)[CH2:2][C:3]#[CH:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 59557712HCID 59557712, compound

Product 1

HCID 25169378HCID 25169378, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (−30° C.) of (3R,4S,5S,6R)-2-(2-((but-3-ynyloxy)methyl)-4-chloro-5-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (BW) (12 mg, 0.0238 mmol) in 0.5 mL of 1:1 CH2Cl2:CH3CN was added Et3SiH (16 μL, 0.1 mmol) followed by addition of BF3.OEt2 (10 μL, 0.0789 mmol). After stirring for about 4 h, the reaction was quenched with a saturated solution of NaHCO3. The solution was extracted with ethyl acetate and the extracts were washed with brine, followed by drying over Na2SO4. The solution was concentrated and the resulting residue was purified by preparative HPLC to afford 3.5 mg of title product. 1H-NMR (CD3OD, 400 MHz) δ 7.47 (s, 1H), 7.45 (s, 1H), 7.10 (s, 4H), 4.80 (d, J=12.4 Hz, 1H), 4.61 (d, J=12.4 Hz, 1H), 4.49 (d, J=8.8 Hz, 1H), 4.10 (d, J=15.0 Hz, 1H), 4.05 (d, J=15.0 Hz, 1H), 3.88 (dd, J=12.0, 2.0 Hz, 1H), 3.70-3.64 (m, 3H), 3.50 (t, J=8.4 Hz, 1H), 3.46-3.40 (m, 3H), 2.60 (q, J=7.4 Hz, 2H), 2.53-2.49 (m, 2H), 2.30 (t, J=2.6 Hz, 1H), 1.21 (t, J=7.4 Hz, 3H); LC-MS (m/z): 475 [M+H]+, 519 [M+HCO2]−.

Workup

  1. customthe reaction was quenched with a saturated solution of NaHCO3
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extracts were washed with brine
  4. dry with materialby drying over Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b8c02dd6ef6f42258cba5f29029b0998
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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