1-Hydroxybenzotriazole → HCID 6482306, compound

HRID 639766Notes

Reaction equation

HRID 639766 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH2:20])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:35])[CH2:30][CH2:31][C:32](O)=[O:33])=[CH:25][CH:24]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:32](=[O:33])[CH2:31][CH2:30][C:29]([C:26]3[CH:25]=[CH:24][C:23]([Cl:22])=[CH:28][CH:27]=3)=[O:35])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 776043-(4-Chlorobenzoyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

Product 1

HCID 6482306HCID 6482306, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

(S)-N-[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl amine (0.100 gm, 0.00034 moles) was taken up in 1:1 THF-water mixture (20 ml). To this was added 4-(4-chlorophenyl)-4-oxobutanoic acid (0.072 g, 0.00034 moles and HOBt (0.046 g, 0.00034 moles). The resulting mixture was cooled to 0° C., and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.071 gm, 0.00037 moles) was added. The resulting mixture was allowed to warm to room temperature and then stirred for 24 hr. The reaction mixture was concentrated and 2 ml of saturated aqueous sodium bicarbonate solution was added, stirred for 15 min and then extracted with dichloromethane. The organic layer was separated and evaporated off. The residue was chromatographed over silica gel (100-200 mesh, 20 g) and eluted with mixture of ethyl acetate:hexane, and finally with ethyl acetate. The combined fractions were concentrated to give (0.070 gm, 42%) of the title compound as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. addition2 ml of saturated aqueous sodium bicarbonate solution was added
  4. stirringstirred for 15 min
  5. extractionextracted with dichloromethane
  6. customThe organic layer was separated
  7. customevaporated off
  8. customThe residue was chromatographed over silica gel (100-200 mesh, 20 g)
  9. washeluted with mixture of ethyl acetate
  10. concentrationThe combined fractions were concentrated

Sources & evidence

ORD record
ord-3f82da78b173489dad42309ca736c1cf
Source dataset
uspto-grants-2010_04
Patent number
US07691889B2

Reaction notes

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