3-Phenylphenol → N-tert-Butoxycarbonyl-trans-4-(3-Biphenyloxy)-L-Proline Methyl Ester

HRID 2185493Notes

Reaction equation

HRID 2185493 reaction equation
[CH3:1]COC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18]([N:20]1[CH2:27][C@H:26]([OH:28])[CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:29]1([C:35]2[CH:36]=[C:37](O)[CH:38]=[CH:39][CH:40]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][O:23][C:22](=[O:24])[C@@H:21]1[CH2:25][C@@H:26]([O:28][C:31]2[CH:30]=[C:29]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:34]=[CH:33][CH:32]=2)[CH2:27][N:20]1[C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19]

Participants

6

Reactant 4

HCID 113813-PhenylphenolHCID 11776TriphenylphosphineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 21341533N-tert-Butoxycarbonyl-trans-4-(3-Biphenyloxy)-L-Proline Methyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethylazodicarboxylate (829 μL) in tetrahydrofuran (10 mL) was added to a cold (−15° C.) stirred solution of N-tert-butoxycarbonyl-trans-4-hydroxy-L-proline (1.23 g), 3-phenylphenol (896 mg), and triphenyl phosphine (1.38 g) in tetrahydrofuran (30 mL) under argon, After stirring at room temperature for 15.5 hr, the solvent was evaporated and coevaporated several times with toluene in vacuo. The residue was diluted with toluene and precipitated solids were removed by filtration, which was washed with toluene. The combined organic layers were evaporated in vacuo and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, v/v) to give title compound (837 mg): 1H-NMR (400 MHz, CDCl3) δ 1.36-1.50 (m, 9H), 2.18-2.29 (m, 1H), 2.51-2.64 (m, 1H), 3.68-3.89 (m, 5H), 4.40-4.56 (m, 1H), 4.91-5.01 (m, 1H), 6.79-6.87 (m, 1H), 7.04-7.10 (m, 1H), 7.17-7.24 (m, 1H), 7.29-7.39 (m, 2H), 7.39-7.49 (m, 2H), and 7.49-7.60 (m, 2H).

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was diluted with toluene
  3. customprecipitated solids
  4. customwere removed by filtration, which
  5. washwas washed with toluene
  6. customThe combined organic layers were evaporated in vacuo
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-f9e90175c4d644828eb67129e09eb16b
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…