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

HRID 1994615노트

반응식

HRID 1994615 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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, 2H), 7.09 (d, J=7.7 Hz, 2H), 5.39 (br s, 1H), 4.48 (t, J=8.4 Hz, 1H), 4.37 (dd, J=8.6, 5.6 Hz, 1H), 4.11-4.06 (m, 1H), 2.86 (d, J=7.1 Hz, 2H), 2.36 (s, 3H).

후처리

  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)

출처 및 근거

ORD 기록
ord-45fd215bf89d4459a1ebdc75cc7ec7b5
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652049B2

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