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

HRID 639764ノート

反応式

HRID 639764 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-b0083032926e45828fc83e38f6953a2f
出典データセット
uspto-grants-2010_04
特許番号
US07691889B2

反応ノート

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