Boron trifluoride etherate → HCID 86728134, compound

HRID 627671Notes

Reaction equation

HRID 627671 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([CH3:23])([CH3:22])[S:20](=[O:25])(=[O:24])[CH2:19][C@:18]([C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=2[F:36])([CH3:26])[N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:47][C:48]1([CH3:51])[CH2:50][O:49]1.B(F)(F)F.CCOCC.[Cl-].[NH4+]>C1COCC1>[C:11]([O:10][C:9]([N:8]([C:16]1[C:21]([CH3:23])([CH3:22])[S:20](=[O:25])(=[O:24])[CH:19]([CH2:47][C:48]([OH:49])([CH3:51])[CH3:50])[C@:18]([C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=2[F:36])([CH3:26])[N:17]=1)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:15])([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 11208Isobutylene oxideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 86728128HCID 86728128, compound

Product 1

HCID 86728134HCID 86728134, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyl N-tert-butoxycarbonyl-N-[(3R)-3-(2-fluoro-5-nitro-phenyl)-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate (0.4 g, 0.756 mmol) in THF (3.8 mL) was cooled to −78° C. and to this was added LHMDS (1.0M in THF; 1.51 ml, 1.51 mmol) dropwise via syringe. The reaction was stirred at −78° C. for 1 hr. 2,2-dimethyloxirane (0.134 ml, 1.51 mmol) was then added followed by BF3.OEt2 (1.44 ml, 1.44 mmol) as a solution in 2 mL of THF. The reaction was stirred at −78° C. for 1 hr. The reaction was treated with aqueous ammonium chloride solution and extracted with ethyl acetate. The organic portion was dried over Na2SO4, filtered, concentrated and purified by column chromatography, eluting with 0-40% EtOAc/Heptanes to give the title compound (376 mg, 0.624 mmol, 83% yield) as a white solid. MS m/z=624.2 (M+Na).

Workup

  1. stirringThe reaction was stirred at −78° C. for 1 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic portion was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. washeluting with 0-40% EtOAc/Heptanes

Sources & evidence

ORD record
ord-55aa3ffc43d640db966311d4bab46afb
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…