Ceric ammonium nitrate → HCID 58109448, compound

HRID 2037566Notes

Reaction equation

HRID 2037566 reaction equation
C[C@@H:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:27])[N:3]1[C@H:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([OH:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1)[CH3:29].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(Cl)Cl.O>[OH:40][C:37]([CH3:38])([CH3:39])[CH2:36][C:33]1[CH:34]=[CH:35][C:30]([C@@H:28]([N:3]2[CH2:2][CH2:7][C@:6]([CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[O:5][C:4]2=[O:27])[CH3:29])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 66856531HCID 66856531, compound

Product 1

HCID 58109448HCID 58109448, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of methyl (R)-3-((S)-1-(4-(2-hydroxy-2-methylpropyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 0.188 mmol) in DCM/H2O (10:1, 2 mL) was added CAN (100 mg). The formed mixture was stirred for 3 h. The reaction was washed with water and extracted with CH2Cl2. The combined organic phase was concentrated to provide the crude product, which was purified by preparative HPLC to give (R)-3-((S)-1-(4-(2-hydroxy-2-methylpropyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (0.8 mg, 10%). LC-MS Method 2 tR=1.191 min, m/z=411.24; 1H NMR (CDCl3): δ=0.81 (m, 4H), 1.09 (d, 6H), 1.43 (d, 3H), 1.64 (m, 3H), 1.92 (m, 3H), 2.16-2.26 (m, 4H), 2.59 (s, 2H), 2.83 (m, 1H), 3.52 (t, 2H), 5.62 (q, 1H), 6.78 (m, 2H), 6.86 (m, 2H), 6.94 (m, 1H), 7.26 (m, 4H).

Workup

  1. washThe reaction was washed with water
  2. extractionextracted with CH2Cl2
  3. concentrationThe combined organic phase was concentrated
  4. customto provide the crude product, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-e59530410deb4ec7b670dc9890bf143a
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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