4-Nitrobenzoic Acid → HCID 178418813, compound

HRID 271335Notes

Reaction equation

HRID 271335 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O.C(OC(N=NC(OC(C)C)=O)=O)(C)C>C1COCC1.C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([OH:14])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178418329HCID 178418329, compound

Product 1

HCID 178418813HCID 178418813, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2.2 g of trans (4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester, 4 g of triphenyl-phosphine, 4.2 g of 4-nitrobenzoic acid, 120 mL of benzene and 10 mL of THF was added 3.5 g of diisopropyl-azo-di-carboxylate over 5 min. The mixture was allowed to stir at room temperature for 4 h and then concentrated under reduced pressure, taken up in 250 mL of dichloromethane and filtered and again concentrated. Chromatography on silica gel eluting with a gradient of 2%-20% ethyl acetate in hexane gave 1.2 g of product as a crystalline solid; 1H NMR (400 MHz, CDCl3) 8.3 (d, 2H), 8.2 (d, 2H), 3.8 (br m, 1H), 3.6 (br m, 1H), 2.4 (d, 1H), 2.1-1.6 (complex m, 8H), 1.45 (s, 9H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered
  3. concentrationagain concentrated

Sources & evidence

ORD record
ord-1bcd75a486fe4bb3bf65b6286249f0c5
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

Loading…