(Diethylamino)sulfur trifluoride → HCID 10870025, compound

HRID 508330Notes

Reaction equation

HRID 508330 reaction equation
O[CH:2]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(N(S(F)(F)[F:26])CC)C.OP([O-])(O)=O.[Na+]>ClCCl>[F:26][CH:2]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 10661075HCID 10661075, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 10870025HCID 10870025, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared as described in Taylor, W P, et. Al, Bioorg. Med. Chem. 4:1515-1520 (1996). The product from Example 30, Part A (500 mg, 1.729 mmol) was dissolved in dichloromethane (10 mL) and treated by drop wise addition of (diethylamino)sulfur trifluoride (DAST) (2.5 mL, 18.9 mmol). The mixture was stirred at room temperature for 18 h. A solution of half saturated sodium phosphate monobasic (20 mL) was added followed by dichloromethane (20 mL) addition and separation of the resulting organic phase. The organic solution was dried and concentrated under vacuum, and then subjected to column chromatography using silica gel eluting with a 1/1 mixture of hexanes/ethyl acetate to provide the title compound as an oil (215 mg, 43%).

Workup

  1. customThe title compound was prepared
  2. customThe organic solution was dried
  3. concentrationconcentrated under vacuum
  4. additionwith a 1/1 mixture of hexanes/ethyl acetate

Sources & evidence

ORD record
ord-c4f2b581d0074468b0a357ed968c2e3b
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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