Ethylene → (S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(dihydroisoxazol-3-yl)propanoyl)oxazolidin-2-one

HRID 1675246Notes

Reaction equation

HRID 1675246 reaction equation
C=C.[CH2:3]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16](=[O:37])[CH2:17][C@@H:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH2:19][N+:20]([O-])=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:38][C:39](OC(OC(OC(C)(C)C)=O)=O)(C)C>C(#N)C.CN(C1C=CN=CC=1)C>[CH2:3]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16](=[O:37])[CH2:17][C@@H:18]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:28]=1)[CH:19]1[CH:39]=[CH:38][O:21][NH:20]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6325EthyleneHCID 90495Di-tert-butyl dicarbonateHCID 57801835(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-4-nitrobutanoyl)oxazolidin-2-one

Product 1

HCID 67330499(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(dihydroisoxazol-3-yl)propanoyl)oxazolidin-2-oneYield 88.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Ethylene was bubbled into 7.3 (882 mg, 1.86 mmol) in 40 mL ACN at room temperature for 20 minutes. (Boc)2O (610 mg, 2.79 mmol) was added at room temperature, followed by the addition of DMAP (23 mg, 0.19 mmol). The mixture was stirred at room temperature for 6 hours. After HPLC indicated that all the 7.3 was consumed, the reaction mixture was taken into EtOAc (500 mL) and saturated sodium bicarbonate (400 mL). The organic layer was separated, washed with brine, dried, and concentrated under vacuum. The crude product was purified by flash chromatography to give 9.1 800 mg). MS ESI (pos.) m/e: 485 (M+H).

Workup

  1. customwas consumed
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-576cf181797d423a9601ebfcef95bff8
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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