4-Nitrophenol → HCID 22852416, compound

HRID 1609766Notes

Reaction equation

HRID 1609766 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:37]([C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1)([O-:39])=[O:38].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@H:7]([O:9][C:43]2[CH:44]=[CH:45][C:40]([N+:37]([O-:39])=[O:38])=[CH:41][CH:42]=2)[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22852416HCID 22852416, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Boc-trans-4-hydroxyproline methyl ester (10.0 g, 41 mmol) 150 mL of anhydrous THF at 0° C. under N2 was added triphenylphosphine (12.7 g, 48 mmol) and 4-nitrophenol (6.7 g, 48 mmol). To this mixture was added diethylazodicarboxylate (7.7 mL, 48 mmol) dropwise over a 30 minute period. The mixture was warmed to room temperature. After stirring for 2 days, the solvent was removed in vacuo, and the crude oil treated successively with 200 mL portions of toluene and ether to remove triphenylphosphine oxide and diethylazodihydrazide by crystallization. The resulting oil was then chromatographed (SiO2, 15-50% ethyl acetate/hexanes) to provide 5.2 g (34%) of N-Boc-4-(cis)-(4-nitrophenoxy)-L-proline methyl ester as a light yellow oil.

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe crude oil treated successively with 200 mL portions of toluene and ether
  3. customto remove triphenylphosphine oxide and diethylazodihydrazide
  4. customby crystallization
  5. customThe resulting oil was then chromatographed (SiO2, 15-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3469f9333b9c40859ad5ed5e6a4b6b10
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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