4-Nitrobenzoic Acid → HCID 86607257, compound

HRID 1437337Notes

Reaction equation

HRID 1437337 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][C@@H:4]([C:16]([NH2:18])=[O:17])[CH2:3]1.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CN(C=O)C>[C:12]([O:11][C:9]([NH:8][C@@H:7]1[CH2:6][CH2:5][C@@H:4]([C:16](=[O:17])[NH2:18])[CH2:3][C@@H:2]1[O:1][C:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58743890HCID 58743890, compound

Product 1

HCID 86607257HCID 86607257, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (1R,3R,4R)-3-hydroxy-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid amide (e) (2.78 g, 10.8 mmol), para-nitrobenzoic acid (2.16 g, 12.9 mmol) and triphenylphosphine (3.38 g, 12.9 mmol) in dry THF (200 mL) and DMF (25 mL) under argon was added dropwise diisopropyl azodicarboxylate (2.5 mL, 12.9 mmol) at 0° C. After 5 min at 0° C. and 17 hours at room temperature, the mixture was concentrated in vacuo and the residue purified by flash column chromatography (silica gel, DCM/MeOH, 0-4%) to give a white solid (2.36 g, 5.8 mmol, 54%).

Workup

  1. concentration17 hours at room temperature, the mixture was concentrated in vacuo
  2. customthe residue purified by flash column chromatography (silica gel, DCM/MeOH, 0-4%)

Sources & evidence

ORD record
ord-14de32859634449daca360950989934b
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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