N,N-Dimethylglycine → HCID 86609335, compound

HRID 459055Notes

Reaction equation

HRID 459055 reaction equation
CNC[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C@H:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:32][C@H:31]([CH2:33][N:34]5[CH:38]=[CH:37][N:36]=[N:35]5)[O:30][C:29]4=[O:39])=[CH:24][C:23]=3[F:40])=[CH:18][N:17]=2)[CH2:12]1)=[O:8].[CH3:41][N:42]([CH3:47])[CH2:43]C(O)=O.C(N=C=NC(C)C)(C)C.[CH3:57][N:58]([CH:60]=[O:61])[CH3:59]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:41][N:42]([CH3:47])[CH2:43][C:60]([N:58]([CH3:59])[CH2:57][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C@H:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:32][C@H:31]([CH2:33][N:34]5[CH:38]=[CH:37][N:36]=[N:35]5)[O:30][C:29]4=[O:39])=[CH:24][C:23]=3[F:40])=[CH:18][N:17]=2)[CH2:12]1)=[O:8])=[O:61]

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 18442996HCID 18442996, compound

Product 1

HCID 86609335HCID 86609335, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

[(5S)-3-(5-{2-fluoro-4[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl 5-(methylamino)pentanoate (Example 37: 134 mg, 0.23 mMol), N,N-dimethylglycine (140 mg, 1.36 mMol), 1,3-diisopropylcarbodiimide (121 mg, 0.96 mMol), and 4-dimethylaminopyridine (5 mg, 0.04 mMol) were suspended in 2 ml of DMF at room temperature. The mixture was stirred one day, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate and evaporated. The residue was purified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane) to give the title compound as the free base. The sample was dissolved in methylene chloride (0.5 ml), treated with HCl (4M solution in dioxane, 0.05 ml) and diluted with diethyl ether (10 ml). The suspension was sonicated and triturated, the solution was decanted from the solids which were resuspended in diethyl ether followed by further sonication then filtration. The solid was dried in vacuo to yield the hydrochloride salt of the title compound as a light yellow solid (95 mg), melting point: 133° C.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8881c325b1a44580a36b3be2ed81e92a
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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