4-Nitrobenzoic Acid → HCID 89666913, compound

HRID 2171265Notes

Reaction equation

HRID 2171265 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.O[CH:47]([CH:58]([CH3:60])[CH3:59])[C@@H:48]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])[CH3:49]>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:47]([CH:58]([CH3:60])[CH3:59])[C@@H:48]([NH:50][C:51]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:57])[CH3:49])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89666915HCID 89666915, compound

Product 1

HCID 89666913HCID 89666913, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzoic acid (10.6 g), triphenylphosphine (20.8 g), and DIAD (42 ml) were added to a THF (50 ml) solution containing tert-butyl ((2S)-3-hydroxy-4-methylpentan-2-yl)carbamate (11.5 g) obtained in the 2nd step, followed by stirring at room temperature for 15 hours. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 5:1). Yellow oily matter of (2S)-2-((tert-butoxycarbonyl)amino)-4-methylpentan-3-yl 4-nitrobenzoate (10 g) was thus obtained.

Workup

  1. customobtained in the 2nd step
  2. distillationThe solvent was distilled away under reduced pressure
  3. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 5:1)

Sources & evidence

ORD record
ord-de373be709644b639a2c5c2457977cc0
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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