Water → (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-(((S)-1-phenylethyl)amino)pyrimidin-4-yl)oxazolidin-2-one

HRID 57472

반응식

HRID 57472 반응식
[C:1]([O:5][C@@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][N:17]=[C:16](F)[N:15]=1)[CH3:7])([CH3:4])([CH3:3])[CH3:2].[C:21]1([C@@H:27]([NH2:29])[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.O>CS(C)=O.CCCCCCC.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:29][C@H:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:28])[N:15]=1)[CH3:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 962WaterHCID 758181-Phenethylamine, (-)-HCID 81531DiisopropylethylamineHCID 90415866(R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoropyrimidin-4-yl)oxazolidin-2-one

생성물 1

HCID 90416117(R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-(((S)-1-phenylethyl)amino)pyrimidin-4-yl)oxazolidin-2-one수율 93%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매HCID 8900Heptane용매

실험 절차

A solution of (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoropyrimidin-4-yl)oxazolidin-2-one (112 mg, 0.40 mmol), (S)-1-phenylethanamine (58 mg, 0.48 mmol, 1.2 equiv), and DIPEA (153 mg, 1.2 mmol, 3.0 equiv) in DMSO (4.0 mL) was heated at 100° C. for 90 min. The reaction mixture was poured into 5 ml of water, extracted with EA (2×10 ml), the solvent was removed to yield the crude product. Silica gel column chromatography (ethyl acetate in heptane 10 to 50%) provided the pure product (142 mg, white solid) in a 93% yield. HRMS m/z 385.2231 (M+H)+, RT=3.35 min.

후처리

  1. extractionextracted with EA (2×10 ml)
  2. customthe solvent was removed
  3. customto yield the crude product

출처 및 근거

ORD 기록
ord-b06878a155664fa0b46e4ee53ebfd747
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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