Boron trifluoride etherate → (3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

HRID 492257Notes

Reaction equation

HRID 492257 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[C@@H:10]2[C@@H:8]([N:9]2[P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=1)=[O:5])[CH3:2].[CH3:26][CH2:27][CH:28]([OH:31])[CH2:29][CH3:30].B(F)(F)F.CCOCC>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[C@@H:10]([NH:9][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])[C@H:8]([O:31][CH:28]([CH2:29][CH3:30])[CH2:27][CH3:26])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 114283-PentanolHCID 44221277(1S,5R,6S)-7-(diethoxy-phosphoryl)-5-methanesulfonyloxy-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid ethyl ester

Product 1

HCID 44221278(3R,4S,5R)-4-(diethoxy-phosphorylamino)-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.94 g of 16 and 3-pentanol (20 mL) cooled to 0-5° C. in a 50 mL round-bottom flask equipped with a magnetic stirrer and an argon gas supply was added 736 μl boron trifluoride ethyl etherate. The reaction mixture was stirred for 16 h at RT and the reaction mixture was then diluted with 50 mL of EtOAc and twice extracted with 70 mL of water. The organic phase was separated, dried (Na2SO4, 25 g) filtered and concentrated in a rotary evaporator at 40° C./70-10 mbar to afford 2.18 g of the crude product as a yellow oil. The crude product was purified by SiO2 column chromatography eluting with tert-butyl methyl ether. The combined fractions were evaporated and dried on a rotary evaporator at 40° C./250-10 mbar to afford 1.47 g of 18 as a light yellow solid.

Workup

  1. customequipped with a magnetic stirrer
  2. extractiontwice extracted with 70 mL of water
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4, 25 g)
  5. filtrationfiltered
  6. concentrationconcentrated in a rotary evaporator at 40° C./70-10 mbar
  7. customto afford 2.18 g of the crude product as a yellow oil
  8. customThe crude product was purified by SiO2 column chromatography
  9. washeluting with tert-butyl methyl ether
  10. customThe combined fractions were evaporated
  11. customdried on a rotary evaporator at 40° C./250-10 mbar

Sources & evidence

ORD record
ord-6884f2ca5cf34a329c710e6b1131b325
Source dataset
uspto-grants-2009_05
Patent number
US07531687B2

Reaction notes

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