4-Nitrobenzoic Acid → [(1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl]4-nitrobenzoate

HRID 1436107Notes

Reaction equation

HRID 1436107 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C@@H:16]([CH3:35])[C@H:17]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:18]1[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=1.[N+:36]([C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1)([O-:38])=[O:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N+:36]([C:39]1[CH:40]=[CH:41][C:42]([C:43]([O:15][C@H:16]([CH3:35])[C@H:17]([NH:27][C:28]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:34])[C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[C:20]([F:26])[CH:19]=2)=[O:44])=[CH:46][CH:47]=1)([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68717988tert-butyl [(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

Product 1

HCID 68911294[(1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl]4-nitrobenzoateYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (6 ml) was added dropwise to a solution of tert-butyl [(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate (5.88 g), 4-nitrobenzoic acid (4.84 g), and triphenylphosphine (7.59 g) in THF (100 ml) under ice-cooling in a nitrogen atmosphere, and the reaction solution was stirred at room temperature for two hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3). Then, the resulting powder was triturated with toluene-hexane to obtain 6.69 g of the title compound.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3)
  4. customThen, the resulting powder was triturated with toluene-hexane

Sources & evidence

ORD record
ord-a11e215ca84e476e864f7cea82a34c1d
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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