Lawesson's reagent → HCID 59953052, compound

HRID 279057Notes

Reaction equation

HRID 279057 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=O)[CH3:28])[O:22][C:21]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:19][CH2:18][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[CH2:10][CH2:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[S:40])[CH3:28])[O:22][C:21]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:19][CH2:18][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 54071786HCID 54071786, compound

Product 1

HCID 59953052HCID 59953052, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred suspension of 32 (0.210 g, 0.500 mmol) in dioxane (5.0 mL), under nitrogen was treated with Lawesson's Reagent (0.202 g, 0.500 mmol), refluxed for 4 h and concentrated in vacuo. The residue was chromatographed on silica gel with mixtures of MeOH—NH4OH—CHCl3 containing 1-10% MeOH and 0.1-0.5% NH4OH and the resulting product was crystallized from MeOH—CHCl3-EtOAc to give 0.0491 g of 3: mp 218.5° C.; HR FAB MS theory for C19H22FN5O4S (M+): 435.1376; found 435.1370. Anal. calcd for C19H22FN5O4S.0.5 H2O: C, 51.34; H, 5.21; N, 15.76. Found: C, 51.69; H, 5.00; N, 15.25.

Workup

  1. temperaturerefluxed for 4 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on silica gel with mixtures of MeOH—NH4OH—CHCl3 containing 1-10% MeOH and 0.1-0.5% NH4OH
  4. customthe resulting product was crystallized from MeOH—CHCl3-EtOAc

Sources & evidence

ORD record
ord-0422783027ca47cbb596cf9291ece72c
Source dataset
uspto-grants-2002_03
Patent number
US06362189B1

Reaction notes

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