1-Hydroxybenzotriazole → HCID 6482313, compound

HRID 639765Notes

Reaction equation

HRID 639765 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.[CH3:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:36])[CH2:31][CH2:32][C:33](O)=[O:34])=[CH:26][CH:25]=1.C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC>C1COCC1.O>[CH3:22][S:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([CH2:31][CH2:32][C:33]([NH:20][CH2:19][C@@H:17]2[O:16][C:15](=[O:21])[N:14]([C:4]3[CH:5]=[CH:6][C:7]([N:8]4[CH2:9][CH2:10][O:11][CH2:12][CH2:13]4)=[C:2]([F:1])[CH:3]=3)[CH2:18]2)=[O:34])=[O:36])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 20637154-[4-(methylthio)phenyl]-4-oxobutanoic 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 6482313HCID 6482313, compoundYield 79%

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 (0.200 gm, 0.00068 moles) was taken up in 1:1 THF-water mixture (20 ml). To this was added 4-(4-methlythiophenyl)-4-oxobutanoic acid (0.152 g, 0.00068 moles and HOBt (0.091 gm, 0.00068 moles) and the resulting mixture was cooled to 0° C., and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.142 g, 0.00074 moles) was added. The resulting mixture was allowed to warm to room temperature and then stirred for 24 hr. The reaction mixture was concentrated, 15 ml of saturated aqueous sodium bicarbonate was added to, stirred for 15 min and then extracted with ethyl acetate. The ethyl acetate layer was separated and evaporated off. The residue was chromatographed over silica gel (100-200 mesh, 20 g). 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 (0.270 gm, 79%) as a white solid.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. addition15 ml of saturated aqueous sodium bicarbonate was added to,
  4. stirringstirred for 15 min
  5. extractionextracted with ethyl acetate
  6. customThe ethyl acetate layer was separated
  7. customevaporated off
  8. customThe residue was chromatographed over silica gel (100-200 mesh, 20 g)
  9. washThe column was eluted with mixture of ethyl acetate
  10. concentrationThe combined fractions were concentrated

Sources & evidence

ORD record
ord-0b2a486cd6044cbbb19323cabbb8807b
Source dataset
uspto-grants-2010_04
Patent number
US07691889B2

Reaction notes

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