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

HRID 16324

Reaction equation

HRID 16324 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([O:19][C:20](=[O:35])[NH:21][C@H:22]([C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=1)[C@@H:23]([OH:25])[CH3:24])([CH3:18])([CH3:17])[CH3:16].[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>[C:15]([O:19][C:20]([NH:21][C@H:22]([C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=1)[C@H:23]([O:25][C:43](=[O:44])[C:42]1[CH:41]=[CH:40][C:39]([N+:36]([O-:38])=[O:37])=[CH:47][CH:46]=1)[CH3:24])=[O:35])([CH3:16])([CH3:17])[CH3:18]

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

In nitrogen atmosphere, diisopropyl azodicarboxylate (6 mL) was dropwise added to a THF solution (100 mL) of [(1R,2S)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester (5.88 g), 4-nitrobenzoic acid (4.84 g), and triphenylphosphine (7.59 g) under ice-cooling. This reaction solution was stirred at room temperature for 2 hr and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3) to give a powder. The obtained powder was triturated with toluene-hexane to give 6.69 g of the title compound. The physical property values of this compound were as follows:

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=97:3)
  4. customto give a powder
  5. customThe obtained powder was triturated with toluene-hexane

Sources & evidence

ORD record
ord-f37635d2a8bc427d9c76141fa1f3a4be
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Linked notes

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