4-Nitrophenol → HCID 131719246, compound

HRID 375120Notes

Reaction equation

HRID 375120 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7](O)[CH2:6][N:5]1C(OC(C)(C)C)=O.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]([OH:46])=[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][CH2:7][CH2:6][N:5]1[O:46][C:43]1[CH:44]=[CH:45][C:40]([N+:37]([O-:39])=[O:38])=[CH:41][CH:42]=1

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 131719246HCID 131719246, compound

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-1a5085c723084d3f9eb6a3b9d8aac7b2
Source dataset
uspto-grants-1996_01
Patent number
US05484780

Reaction notes

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