Tetrahydrofuran → (4R)-3-((3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

HRID 1662572노트

반응식

HRID 1662572 반응식
C(OC(OC(C)(C)C)=O)(O[C:4](C)(C)[CH3:5])=O.[N+:16]([CH2:19][C@@H:20]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:38]=1)[CH2:21][C:22]([N:24]1[C@H:28]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:27][O:26][C:25]1=[O:36])=[O:23])([O-])=[O:17].C(Br)=C.C1COCC1>CN(C)C1C=CN=CC=1.CCOC(C)=O>[O:17]1[CH:5]=[CH:4][C:19]([C@@H:20]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:38]=2)[CH2:21][C:22]([N:24]2[C@H:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:27][O:26][C:25]2=[O:36])=[O:23])=[N:16]1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 11641BromoetheneHCID 90495Di-tert-butyl dicarbonateHCID 57706543(4R)-3-((3R)-4-Nitro-3-(3-((phenylmethyl)oxy)phenyl)butanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

생성물 1

HCID 57706758(4R)-3-((3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one수율 75.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

At room temperature, di-t-butyl dicarbonate (0.502 g, 2.30 mmol) was added to a solution of (R)-4-benzyl-3-((R)-3-(3-(benzyloxy)phenyl)-4-nitrobutanoyl)oxazolidin-2-one (94.1B) (0.727 g, 1.53 mmol), vinyl bromide, (1.0 M solution in THF (16.9 mL, 16.9 mmol), N,N-dimethylpyridin-4-amine (DMAP) (0.0187 g, 0.153 mmol) and TEA (0.256 mL, 1.84 mmol). The mixture was stirred at room temperature for 24 hours. The reaction was then diluted with EtOAc (200 mL) and washed with sodium bicarbonate solution and brine. The organic phase was dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:2 EtOAc/hexane) and gave 558 mg of 94.1C.

후처리

  1. washwashed with sodium bicarbonate solution and brine
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customAfter removing solvent
  4. customthe residue was purified by flash chromatography (silica gel, 1:2 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-0062dd5d02c74e3c9977ec5de3a01767
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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