Lawesson's reagent → HCID 69733914, compound

HRID 488373Notes

Reaction equation

HRID 488373 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)[CH2:18]N(C(OC)=O)C[CH2:15]3)[CH2:7]1)(=[O:3])[CH3:2].[CH3:26][O:27]C1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>>[CH2:15]1[C:14]2[CH:13]=[C:12]([N:8]3[CH2:7][C@H:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])[O:10][C:9]3=[O:11])[CH:21]=[CH:20][C:19]=2[CH2:18][CH2:26][O:27]1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 60054152HCID 60054152, compound

Product 1

HCID 69733914HCID 69733914, compound

Procedure

Following the general procedure of Example 5, and making non-critical variations but substituting (−)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide (Step 4) for methyl 6-[(5S)-5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate, using 0.7 mol-equivalents of Lawesson's reagent and repurifying the product by trituration with MeOH/Et2O or recrystallization from EtOAc/hexane, the title compound is obtained (84%) as a white solid, mp 165° C. (decomp.). MS (ESI+) for C15H18N2O3S m/z 307 (M+H)+; [α]25D=6° (c 0.96, DMSO).

Workup

  1. customrepurifying the product by trituration
  2. customwith MeOH/Et2O or recrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-7abf58bf77264943bf7936abd0c8cb47
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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