Lawesson's reagent → HCID 10288183, compound

HRID 2306626Notes

Reaction equation

HRID 2306626 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:27][C:28](=[O:51])[NH:29][CH2:30][C@@H:31]1[O:35][C:34](=[O:36])[N:33]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[S:44][CH2:45][C:46](=O)[NH:47][N:48]=3)=[C:39]([F:50])[CH:38]=2)[CH2:32]1)([CH3:26])([CH3:25])[CH3:24]>O1CCOCC1>[C:23]([O:27][C:28](=[O:51])[NH:29][CH2:30][C@@H:31]1[O:35][C:34](=[O:36])[N:33]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[S:44][CH2:45][C:46](=[S:10])[NH:47][N:48]=3)=[C:39]([F:50])[CH:38]=2)[CH2:32]1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 60066061HCID 60066061, compound

Product 1

HCID 10288183HCID 10288183, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Lawesson's reagent (0.0715 g, 0.177 mmol) and {3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-carbamic acid tert-butyl ester (0.100 g, 0.236 mmol) in dioxane (5 ml) are heated at 65° C. for 6 hours. The reaction mixture is evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give bright yellow solid (0.088 g, 85%); 1HNMR (300 MHz, DMSO-d6) δ 1.34 (s, 9H), 3.28 (t, J=5.5 Hz, 2H), 3.82 (dd, J=6.0, 9.1 Hz, 1H), 4.01 (s, 2H), 4.14 (t, J=9.3 Hz, 1H), 4.70-4.78 (m, 1H), 7.24 (t, J=5.8 Hz, 1H), 7.45 (dd, J=2.2, 8.8 Hz, 1H), 7.60 (dd, J=2.2, 14 Hz, 1H), 7.73 (t, J=8.8 Hz, 1H), 8.07 (t, J=6.0 Hz, 1H); mp 134-6; MS (m/z): [M+H]+=441.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue is purified by PTLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-b9c64964b6384c2097a1271e4e12ecff
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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