Water → HCID 11291060, compound

HRID 1435705Notes

Reaction equation

HRID 1435705 reaction equation
[Cl:1][C:2]1[C:3]([CH3:20])=[C:4]([S:8]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][CH2:18]O)[N:16]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:41].O>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:20])=[C:4]([S:8]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][CH2:18][Cl:41])[N:16]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 87545745HCID 87545745, compound

Product 1

HCID 11291060HCID 11291060, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of EXAMPLE 181A (100 mg, 0.30 mmol), triphenylphosphine (158 mg, 0.60 mmol) and carbontetrachloride (116 mg, 0.75 mmol) in DMF (2 mL) was stirred over night, and was then poured into water. The mixture was extracted with EtOAc, dried (Sodium sulfate) and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel gradient eluting with 2-4% acetone in DCM giving a solid (25 mg, 24%). 1H NMR (CDCl3) δ 2.64 (s, 3H), 3.17 (t, 2H), 3.77 (t, 2H), 6.30 (s, 1H), 7.24 (m, 2H), 7.56 (d, 1H), 8.02 (d, 1H); MS (Ionspray, [M+H]+) m/z 350.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried (Sodium sulfate)
  3. customthe solvent was evaporated
  4. customThe crude material was purified by flash chromatography on silica gel gradient
  5. washeluting with 2-4% acetone in DCM giving a solid (25 mg, 24%)

Sources & evidence

ORD record
ord-56bc3d78d6a04aaa95ea4aa64d41cd18
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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