Sodium Sulfate → HCID 86701262, compound

HRID 2276063Notes

Reaction equation

HRID 2276063 reaction equation
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][OH:18])[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:30]N(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[O-]S([O-])(=O)=O.[Na+].[Na+].F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl.CCOC(C)=O>[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][O:18][CH3:30])[C:14](=[O:19])[O:13][CH2:12][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:10](=[O:28])[O:9][C@H:8]1[CH3:29])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 86701260HCID 86701260, compound

Product 1

HCID 86701262HCID 86701262, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

A round bottom flask was charged with (3S,6S,7R,8R)-3-(tert-butoxycarbonyl-amino)-8-(2-hydroxyethyl)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (200 mg, 0.48 mmol), Proton Sponge™ (700 mg, 4.05 mmol), Na2SO4 in CH2Cl2 (10 mL) at 0° C. To the resulting suspension was added trimethyloxonium tetrafluoroborate (Me3OBF4, 320 mg, 2.16 mmol), and the suspension was warmed to room temperature (about 22° C.) and stirred for 5 h. The mixture was diluted with EtOAc, filtered, and the filtrate was washed successively with water and 1M NaHSO4. The organics were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. Purification of the crude product via column chromatography (hexanes/EtOAc gradient) afforded the title compound (140 mg, 71%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 5.41-5.16 (m, J=0.9 Hz, 2H), 5.06 (t, J=9.9 Hz, 1H), 4.94-4.73 (m, 2H), 3.69-3.52 (m, 1H), 3.42-3.27 (m, 2H), 3.26 (s, J=0.9 Hz, 3H), 2.80-2.67 (m, 1H), 2.60 (dt, J=13.9, 7.0 Hz, 1H), 2.08-1.86 (m, 1H), 1.66-1.55 (m, 1H), 1.45 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H); ESIMS m/z 454 ([M+Na]+).

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed successively with water and 1M NaHSO4
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification of the crude product via column chromatography (hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-cd8940b0ccb3437a9b35c63b791030b5
Source dataset
uspto-grants-2015_09
Patent number
US09131690B2

Reaction notes

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