Pyridine → HCID 69982285, compound

HRID 1167499Notes

Reaction equation

HRID 1167499 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@@H:5]([C:7](Cl)=[O:8])[CH2:4][O:3]1.Cl.[S:12]1[N:16]=[CH:15][C:14]([O:17][CH2:18][C@@H:19]2[O:23][C:22](=[O:24])[N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH:32]=4)=[C:27]([F:37])[CH:26]=3)[CH2:20]2)=[N:13]1.N1C=CC=CC=1>ClCCl>[S:12]1[N:16]=[CH:15][C:14]([O:17][CH2:18][C@@H:19]2[O:23][C:22](=[O:24])[N:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH2:36][CH2:35][N:34]([C:7]([C@H:5]5[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]5)=[O:8])[CH2:33][CH:32]=4)=[C:27]([F:37])[CH:26]=3)[CH2:20]2)=[N:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10374772(R)-2,2-dimethyl-1,3-dioxolan-4-ylcarbonyl chlorideHCID 69983039HCID 69983039, compound

Product 1

HCID 69982285HCID 69982285, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)-2,2-dimethyl-1,3-dioxolan-4-ylcarbonyl chloride (S Handa et al, Synth. Commun. (1995), 25, 2837) [0.597 g, 3.63 mmol ] in dichloromethane (5 ml) was added dropwise to a stirred mixture of 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-(3-fluoro-4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one hydrochloride (1 g, 2.42 mmol) and pyridine (0.49 ml, 6.06 mmol) in dichloromethane (30 ml) under nitrogen at −10° C. After 10 minutes the cooling bath was removed and the mixture stirred for a further hour. Water (30 ml) was added and the organic layer washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with ether and filtered to give 5(R)-1,2,5-thiadiazol-3-yloxymethyl-3-(4-(1-(2,2-dimethyl-1,3-dioxolan-4(R)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one as a solid (1.13 g, 93%) MS: 504 (MH+); NMR: 1.32 (6H, s); 2.42 (2H+DMSO); 3.7 (2H, m); 4.0 (1H, m); 4.11 (2H, m); 4.25 (2H, m); 4.8 (2H, m); 4.91 (1H, m); 5.12 (1H, m); 6.02 (1H, s); 7.29-7.43 (2H, m); 7.5 (1H, d); 8.42 (1H, s).

Workup

  1. customAfter 10 minutes the cooling bath was removed
  2. additionWater (30 ml) was added
  3. washthe organic layer washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ef011124fe034038af13e42e86f8426c
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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