3-Methoxypropionic acid → HCID 58758409, compound

HRID 459034Notes

Reaction equation

HRID 459034 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH2:18][C@@H:17]([CH2:19][OH:20])[O:16][N:15]=2)=[CH:12][CH:13]=1.[CH3:33][O:34][CH2:35][CH2:36][C:37](O)=O.Cl.CN(C)CCCN=C=NCC.ClCCl.C[CH2:56][O:57]CC>CN(C)C1C=CN=CC=1.CN(C=O)C.C(OCC)(=O)C>[CH3:33][O:34][CH2:35][CH2:36][CH2:37][C:56]([O:20][CH2:19][C@H:17]1[O:16][N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:21]4[CH2:25][C@H:24]([CH2:26][N:27]5[CH:31]=[CH:30][N:29]=[N:28]5)[O:23][C:22]4=[O:32])=[CH:3][C:2]=3[F:1])=[CH:9][N:10]=2)[CH2:18]1)=[O:57]

Participants

8

Reactant 4

HCID 1344423-Methoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9932836(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 58758409HCID 58758409, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1, 0.125 g, 0.29 mmol), 3-methoxypropionic acid (0.13 g, 1.1 mmol), 4-dimethylaminopyridine (0.003 g, 0.025 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.125 g, 0.65 mmol) were combined in DMF (2 ml). The suspension was allowed to stir for 1.5 hours at room temperature resulting in a clear solution. The mixture was then diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The residue obtained upon filtration and evaporation was sonnicated with a solution of dichloromethane:ether (1:5) to give a solid which was dried collected and dried in vacuo. The title compound was obtained as a white solid (0.15 g), melting point: 154° C.

Workup

  1. customresulting in a clear solution
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe residue obtained upon filtration and evaporation
  5. customto give a solid which
  6. customwas dried
  7. customcollected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c8242b08110042afb01c1c70c2bba162
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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