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

HRID 1662572Notes

Reaction equation

HRID 1662572 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0062dd5d02c74e3c9977ec5de3a01767
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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