1-Hydroxybenzotriazole → HCID 131728038, compound

HRID 639763Notes

Reaction equation

HRID 639763 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.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1C(CC=O)C(O)=O.C1C=CC2N([OH:48])N=NC=2C=1.Cl.CN(C)[CH2:52][CH2:53][CH2:54]N=C=NCC.[C:61](=O)(O)[O-:62].[Na+]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:61](=[O:62])[CH2:54][CH2:53][C:52]([C:30]3[C:31]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:27]=[CH:28][CH:29]=3)=[O:48])[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

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinoneHCID 19774789HCID 19774789, compound

Product 1

HCID 131728038HCID 131728038, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

(S)-N-[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl amine (0.200 gm, 0.00068 moles) was taken up in 1:1 dichloromethane-water mixture (10 ml). To this was added 4-(2-naphthyl-4-oxobutanoic acid (0.154 gm, 0.00068 moles and HOBt (0.091 gm, 0.00068 moles) the resulting mixture was cooled to 0° C. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.142 gm, 0.00074 moles) was added the resulting mixture was allowed to warm to room temperature and then stirred for 24 hr. Saturated aqueous sodium bicarbonate solution (2 ml) was added to the reaction mixture, stirred for 15 min and then the organic layer separated and the solvent evaporated off. The residue was chromatographed over silica gel (100-200 mesh, 20 gm). The column was eluted with mixture of ethyl acetate:hexane, and finally with ethyl acetate. The combined fractions were concentrated to give the title compound (0.22 gm, 64%) as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 15 min
  3. customthe organic layer separated
  4. customthe solvent evaporated off
  5. customThe residue was chromatographed over silica gel (100-200 mesh, 20 gm)
  6. washThe column was eluted with mixture of ethyl acetate
  7. concentrationThe combined fractions were concentrated

Sources & evidence

ORD record
ord-d578aeffd29a42f18c5a9dcddb3d2f1f
Source dataset
uspto-grants-2010_04
Patent number
US07691889B2

Reaction notes

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