Lawesson's reagent → HCID 86585980, compound

HRID 1935620Notes

Reaction equation

HRID 1935620 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C@H:17]([CH3:32])[CH2:16][CH2:15]3)[CH2:7]1)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C@H:17]([CH3:32])[CH2:16][CH2:15]3)[CH2:7]1)(=[S:42])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86585981HCID 86585981, compound

Product 1

HCID 86585980HCID 86585980, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product of EXAMPLE 14, Step 2 (1.0 g, 2.3 mmol) and Lawesson's Reagent (0.50 g, 1.3 mmol) are stirred in Toluene (20 mL) at reflux for 2 hours. Solvent is removed by evaporation and the residue is chromatographed on silica gel using 0-4% MeOH/CH2Cl2 eluant. The title compound is isolated as a white solid 1.0 g (97%); HRMS (FAB) calcd for C24H27N3O4S+H1 454.1800, found 454.1813.

Workup

  1. temperatureat reflux for 2 hours
  2. customSolvent is removed by evaporation
  3. customthe residue is chromatographed on silica gel using 0-4% MeOH/CH2Cl2 eluant

Sources & evidence

ORD record
ord-f4c7dfbe076d48a2b1cfabf899c66048
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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