Lawesson's reagent → HCID 131722425, compound

HRID 1531910Notes

Reaction equation

HRID 1531910 reaction equation
[CH:1]1[C:13]2[CH:12]([C:14]3[C:15](=O)[NH:16][C:17](=[O:31])[N:18]([CH2:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([O:26][CH3:27])=[O:25])[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>O1CCCC1>[CH:1]1[C:13]2[CH:12]([C:14]3[C:15](=[S:42])[NH:16][C:17](=[O:31])[N:18]([CH2:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([O:26][CH3:27])=[O:25])[CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 131722426HCID 131722426, compound

Product 1

HCID 131722425HCID 131722425, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from step (iv) (0.3 g) and Lawesson's reagent (0.286 g) in tetrahydrofuran (8 ml) was heated at reflux for 6 hours then cooled and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography eluting with 30-40% ethyl acetate in isohexane.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperaturethen cooled
  4. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customPurified by chromatography
  8. washeluting with 30-40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-836fb42bda4445b296deb6d9f97838ef
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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