1-Hydroxybenzotriazole → (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]-4-oxo-4-(2-thienyl)butanamide

HRID 639764노트

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HRID 639764 반응식
[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.[O:22]=[C:23]([C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)[CH2:24][CH2:25][C:26](O)=[O:27].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:26](=[O:27])[CH2:25][CH2:24][C:23](=[O:22])[C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[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

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 783853-(2-Thenoyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10780199(5S)-5-(Aminomethyl)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxazolidinone

생성물 1

HCID 6482311(S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]-4-oxo-4-(2-thienyl)butanamide수율 56%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

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온도
0 °C

실험 절차

(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-oxo-4 (2-thienyl)butanoic acid (0.125 gm, 0.00068 moles) and HOBt (0.091 gm, 0.00068 moles). The resulting mixture was cooled to 0° C. and then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.142 gm, 0.00074 moles) was added and the resulting mixture was allowed to warm to room temp and then stirred for 24 hr. The reaction mixture was concentrated, 15 ml of saturated sodium bicarbonate was added, stirred for 15 min and then extracted with ethyl acetate. The ethyl acetate layer was 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 (0.175 gm, 56%) as a white solid.

후처리

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

출처 및 근거

ORD 기록
ord-b0083032926e45828fc83e38f6953a2f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691889B2

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