Pyridine → HCID 69366396, compound

HRID 723796Notes

Reaction equation

HRID 723796 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.[NH:12]1[CH2:17][CH2:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][C@H:27]([CH2:29][N:30]4[N:34]=[N:33][CH:32]=[N:31]4)[O:26][C:25]3=[O:35])=[CH:20][C:19]=2[F:36])=[CH:14][CH2:13]1.N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([C:7]([N:12]2[CH2:17][CH2:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:28][C@H:27]([CH2:29][N:30]5[N:34]=[N:33][CH:32]=[N:31]5)[O:26][C:25]4=[O:35])=[CH:20][C:19]=3[F:36])=[CH:14][CH2:13]2)=[O:8])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10374773HCID 10374773, compoundHCID 69363542HCID 69363542, compound

Product 1

HCID 69366396HCID 69366396, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4S)-2,2-Dimethyl-1,3-dioxolane-4-carbonyl chloride (350 mg, 2.10 mM) was added dropwise to a stirred suspension of (5R)-3-(4-(1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(tetrazol-2-ylmethyl)oxazolidin-2-one hydrochloride (500 mg, 1.31 mM) and pyridine (0.52 g, 6.57 mM) in dichloromethane (20 ml) with ice/water cooling. The reaction was allowed to warm to room temperature and stirred 1 hour. The resulting solution was washed with water and saturated brine, dried (magnesium sulfate) and evaporated to a small volume. Addition of diethyl ether gave the title compound (600 mg) as a yellow solid.

Workup

  1. washThe resulting solution was washed with water and saturated brine
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated to a small volume
  4. additionAddition of diethyl ether

Sources & evidence

ORD record
ord-3728f6b229a948b5a846547fdc681977
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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