4-Nitrobenzoic Acid → HCID 67639590, compound

HRID 399524Notes

Reaction equation

HRID 399524 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([C:30]2[CH:35]=[CH:34]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:36]([C:39]1[CH:47]=[CH:46][C:42]([C:43]([OH:45])=O)=[CH:41][CH:40]=1)([O-:38])=[O:37].N(C(OCC)=O)=N[C:50](OCC)=O>C1C=CC=CC=1>[C:35]([O:11][C:10](=[O:12])[C@@H:9]1[CH2:13][C@H:14]([O:16][C:43](=[O:45])[C:42]2[CH:41]=[CH:40][C:39]([N+:36]([O-:38])=[O:37])=[CH:47][CH:46]=2)[CH2:15][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH3:34])([CH3:30])[CH3:50]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 67639590HCID 67639590, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline (500 mg, 1.74 mmol) in benzene (20 mL) were added triphenylphosphine (548 mg, 2.09 mmol), p-nitrobenzoic acid (349 mg, 2.09 mmol), and diethyl azodicarboxylate (364 mg, 2.09 mmol). The reaction mixture was stirred for 1 hour at 80° C. and then evaporated. Flash silica gel chromatography eluting with 0.5% methanol/dichloromethane gave the desired product in 77% yield (581 mg). 400 MHz 1H NMR (CDCl3): δ1.38-1.47 (3s, 18H); 2.37 (m, 1H); 2.49-2.61 (m, 1H); 5.53 (m, 1H); 8.16-8.27 (m, 4H, Ar).

Workup

  1. customevaporated
  2. washFlash silica gel chromatography eluting with 0.5% methanol/dichloromethane

Sources & evidence

ORD record
ord-05c38b36578f48dcb6b8b21b773b71d0
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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