Hexane → HCID 66639408, compound

HRID 1094453Notes

Reaction equation

HRID 1094453 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH:11]([CH2:21][C:22]2[N:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24]([OH:26])=[O:25])[O:10][C:9]1([CH3:32])[CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:33][Si](C=[N+]=[N-])(C)C.CCCCCC>C1C=CC=CC=1.CO>[CH3:33][O:25][C:24](=[O:26])[C:23]1[CH:27]=[CH:28][CH:29]=[N:30][C:22]=1[CH2:21][C@@H:11]1[O:10][C:9]([CH3:32])([CH3:31])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:12]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20]

Participants

6

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 66638811HCID 66638811, compound

Product 1

HCID 66639408HCID 66639408, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-[(R)-3-tert-butoxycarbonyl-4-(2-fluoro-benzyl)-2,2-dimethyl-oxazolidin-5-ylmethyl]-nicotinic acid (11 g, 25 mmol) in 200 mL of benzene and 30 mL of methanol is added a 2M solution of trimethylsilyl-diazomethane in hexane (16 mL, 32 mmol). The reaction is allowed to stir for 1 hour at RT after which time the solvent is removed under reduced pressure. Purification of the resultant residue by silica gel flash column chromatography gives the title compound.

Workup

  1. customis removed under reduced pressure
  2. customPurification of the resultant residue by silica gel flash column chromatography

Sources & evidence

ORD record
ord-036b84a2a52f4757ad8f1f00135cb8c2
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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