Methyl iodide → HCID 69083836, compound

HRID 2362455Notes

Reaction equation

HRID 2362455 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C@@H:15]3[C@@H:19]([C:20]4[NH:24][N:23]=[N:22][N:21]=4)[O:18][C:17](=[O:25])[NH:16]3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26](=O)([O-])[O-].[K+].[K+].IC>O1CCCC1>[CH3:26][N:22]1[N:23]=[N:24][C:20]([C@H:19]2[O:18][C:17](=[O:25])[NH:16][C@@H:15]2[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:10]=2)=[N:21]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178517873HCID 178517873, compound

Product 1

HCID 69083836HCID 69083836, compoundYield 11,785.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4R,5S)-4-(3-(phenylethynyl)phenyl)-5-(1H-tetrazol-5-yl)oxazolidin-2-one (18.6 mg, 0.056 mmol) in tetrahydrofuran (5 mL) was added potassium carbonate (38.8 mg, 0.281 mmol) and iodomethane (0.035 mL, 0.561 mmol) and the reaction mixture was held at 50° C. for 6 hours. The reaction mixture was concentrated and purified by Preparative HPLC Method 16 providing (4R,5S)-5-(2-methyl-2H-tetrazol-5-yl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one (2.4 mg, 6.60 mmol, 11.76% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 4.43 (s, 3H) 5.27 (s, 1H) 5.75 (s, 1H) 7.39-7.46 (m, 4H) 7.49 (t, J=7.63 Hz, 1H) 7.55-7.62 (m, 3H) 8.69 (s, 1H). Mass spec.: 344.11 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-b13bffa3e6d7415d99474308d9bcacfd
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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