Pyridine → (5R)-3-(4-(1-((4S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl)-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723791Notes

Reaction equation

HRID 723791 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([N:15]3[CH2:19][C@H:18]([CH2:20][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)[O:17][C:16]3=[O:26])=[CH:10][C:9]=2[F:27])=[CH:4][CH2:3]1.N1C=CC=CC=1.[CH3:34][C:35]1([CH3:43])[O:39][C@H:38]([C:40](Cl)=[O:41])[CH2:37][O:36]1>ClCCl>[CH3:34][C:35]1([CH3:43])[O:39][C@H:38]([C:40]([N:2]2[CH2:7][CH2:6][C:5]([C:8]3[C:9]([F:27])=[CH:10][C:11]([N:15]4[CH2:19][C@H:18]([CH2:20][N:21]5[CH:25]=[CH:24][N:23]=[N:22]5)[O:17][C:16]4=[O:26])=[CH:12][C:13]=3[F:14])=[CH:4][CH2:3]2)=[O:41])[CH2:37][O:36]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10374773HCID 10374773, compoundHCID 69364600HCID 69364600, compound

Product 1

HCID 69364522(5R)-3-(4-(1-((4S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl)-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (5R)-3-(4-(1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one hydrochloride (650 mg, 1.64 mM) in dry dichloromethane (20 ml) at 0–4°, was treated with pyridine (648 mg, 8.2 mM) followed by dropwise addition of (4S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl chloride (430 mg, 2.64 mM). The solution was allowed to warm to ambient temperature and stir for 1 hour. The reaction mixture was washed with water and brine, dried (sodium sulfate) and evaporated to a gum which crystallised readily on trituration with diethyl ether to give the title compound (788 mg).

Workup

  1. washThe reaction mixture was washed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. customevaporated to a gum which
  4. customcrystallised readily on trituration with diethyl ether

Sources & evidence

ORD record
ord-e4e607c6e4654547a8f9cf17b439a9a7
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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