Diisopropylethylamine → (4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one

HRID 1028647ノート

反応式

HRID 1028647 の反応式
[NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH2:3][OH:4].C(N(C(C)C)CC)(C)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C@H:2]2[CH2:3][O:4][C:23](=[O:25])[NH:1]2)=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 28804561(S)-b-Amino-4-methylbenzenepropanol

生成物 1

HCID 60010750(4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A stirred solution of (2S)-2-amino-3-(4-methylphenyl)propan-1-ol (Step A, 460 mg, 2.79 mmol) in CH2Cl2 (20 mL) at 0° C. was treated with diisopropylethylamine (2.92 mL, 16.74 mmol) and triphosgene (414 mg, 1.39 mmol) under an atmosphere of N2. The reaction stirred at 0° C. for 3 h. The reaction was quenched with sat. NaHCO3 (10 mL) and extracted with EtOAc (4×20 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient) to afford (4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as a white solid. LCMS=192.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.17 (d, J=8 Hz, 2 H), 7.09 (d, J=7.7 Hz, 2 H), 5.39 (br s, 1 H), 4.48 (t, J=8.4 Hz, 1 H), 4.37 (dd, J=8.6, 5.6 Hz, 1 H), 4.11-4.06 (m, 1 H), 2.86 (d, J=7.1 Hz, 2 H), 2.36 (s, 3 H).

後処理

  1. customThe reaction was quenched with sat. NaHCO3 (10 mL)
  2. extractionextracted with EtOAc (4×20 mL)
  3. washThe combined organic layers were washed with brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient)

出典と根拠

ORDレコード
ord-1b530d3c5baa4f108abb922b5394a9cf
出典データセット
uspto-grants-2014_05
特許番号
US08735435B2

反応ノート

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