Boron trifluoride etherate → HCID 86631207, compound

HRID 2275465Notes

Reaction equation

HRID 2275465 reaction equation
C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[C:17]([O-:20])([OH:19])=[O:18].[Na+].ClCCl.[C:25](#[N:27])[CH3:26]>>[C:25](#[N:27])[CH3:26].[C:17](=[O:18])([O-:20])[O-:19].[NH4+:27].[NH4+:27]

Participants

5

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 21877088Acetonitrile methylene chloride

Product 1

HCID 86631207HCID 86631207, compound

Conditions

Temperature
-5 °C

Procedure

One-step procedure: To a solution of 20 mg of cyclic depsipeptide according to formula (II) and 0.027 mL triethylsilane in 2 mL of dichloromethane/acetonitrile (1:1) at −50° C. 0.014 mL of boron trifluoride etherate were slowly added. The reaction mixture was allowed to warm up to −5° C. and kept at this temperature for additional 30 minutes, poured into a saturated NaHCO3 solution, and was extracted with EtOAc. The organic layer was dried over sodium sulfate and the solvent was removed in vacuo. Purification of the residue obtained by HPLC(XTerra [5 cm]; acetonitrile/ammonium carbonate buffer pH10 gradient) provided 9.8 mg of a derivative of the cyclic depsipeptide according to formula (II) wherein the Ahp has been converted into 3-amino-piperidin-2-one. ESI MS: 935.36 [M+Na]+. b) Two-step procedure: To a solution of 1 g of cyclic depsipeptide according to formula (II) in 300 mL of dichloromethane/acetonitrile (1:1) at −50° C. 0.68 mL of boron trifluoride etherate were slowly added. The reaction mixture was allowed to warm up to −20° C. Then additional 0.68 mL of boron trifluoride etherate were slowly added the reaction mixture kept at this temperature until no more starting material could be observed (HPLC). Then the reaction mixture was poured into a saturated NaHCO3 solution, and was extracted with EtOAc. The organic layer was dried over sodium sulfate and the solvent was removed in vacuo providing a derivative of the cyclic depsipeptide according to formula (II) wherein the Ahp has been converted into 3-amino-3,4-dihydro-1H-pyridin-2-one. ESI MS: 933.28 [M+Na]+.

Workup

  1. customat −50° C
  2. extractionwas extracted with EtOAc
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customPurification of the residue
  6. customobtained by HPLC(XTerra [5 cm]

Sources & evidence

ORD record
ord-8a8d32ae03d14cecb0833f7ce0a160bd
Source dataset
uspto-grants-2015_09
Patent number
US09127044B2

Reaction notes

Loading…