4-Nitrobenzoic Acid → HCID 68702128, compound

HRID 1024118Notes

Reaction equation

HRID 1024118 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH2:24][CH2:25][CH2:26][C@H:27]2[CH2:31][CH2:30][CH:29]=[C:28]2[C:32]2[CH:37]=[CH:36][C:35]([C@@H:38]([OH:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:34][CH:33]=2)=[CH:22][CH:23]=1)=[O:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N+:64]([C:67]1[CH:75]=[CH:74][C:70]([C:71](O)=[O:72])=[CH:69][CH:68]=1)([O-:66])=[O:65].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][O:16][C:17]([C:19]1[S:20][C:21]([CH2:24][CH2:25][CH2:26][C@H:27]2[CH2:31][CH2:30][CH:29]=[C:28]2[C:32]2[CH:33]=[CH:34][C:35]([C@H:38]([O:44][C:71](=[O:72])[C:70]3[CH:69]=[CH:68][C:67]([N+:64]([O-:66])=[O:65])=[CH:75][CH:74]=3)[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:36][CH:37]=2)=[CH:22][CH:23]=1)=[O:18]

Participants

7

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 516892Sodium BicarbonateHCID 24997809HCID 24997809, compound

Product 1

HCID 68702128HCID 68702128, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (DIAD, 53 μL, 0.27 mmol) in 1 mL THF was cannula transferred to an ice cold solution of 43 (46 mg, 0.11 mmol), Ph3P (66 mg, 0.25 mmol) and 4-nitrobenzoic acid (50 mg, 0.30 mmol). The solution was allowed to warm to room temperature and after 2.5 h, 20 mL saturated NaHCO3 solution was added. The resulting mixture was extracted with ethyl acetate (2×25 mL) and the combined solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography using a Combiflash unit by Teledyne Isco (12 g silica gel, 0%→15% ethyl acetate/hexanes) to give the title compound (40 mg, 0.069 mmol, 63%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×25 mL)
  2. dry with materialthe combined solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-beb960ef75304c70b9373587581850dd
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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