Ethyl Acetate → HCID 15222088, compound

HRID 274818Notes

Reaction equation

HRID 274818 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8](C)([CH2:47][CH2:48][CH3:49])[NH:7][C:6]=1O)=[O:4].[C:52](OCC)(=[O:54])C>C1COCC1.O=[Mn]=O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([C:28]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([CH2:47][CH2:48][CH3:49])=[N:7][C:6]=1[CH:52]=[O:54])=[O:4]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 178439605HCID 178439605, compound

Product 1

HCID 15222088HCID 15222088, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 10.00 g (14.82 mmole) of 5-methoxycarbonyl-4-hydroxy-methyl-2-propyl-1-[(2'-(N-trityltetrazol-5-yl)biphen-4-yl)methyl]imidazole (Example 101, Part A) in 200 mL THF was added to a stirring slurry of 12.88 g (148.2 mmole) of MnO2 at room temperature. The mixture was stirred at room temperature for 2 days. 3.22 g (37.0 mmole) of additional MnO2 was added to the mixture and stirred at room temperature for 5 hours after which TLC (ethyl acetate) showed no starting material. The product was filtered through Celite™, and the cake was washed with ethyl acetate and methylene chloride; the filtrate was evaporated under reduced pressure to give 8.10 g (81%) of the title compound as a light-yellow-colored solid. 1H NMR (300 MHz, CDCl3): δ 0.89 (t, J=7.3 Hz, 3H); 1.74 (m, 2H); 2.58 (t, J=7.7 Hz, 2H); 3.81 (s 3H); 5.49 (s, 2H); 6.74-7.92 (m, 23H); 10.38 (s, 1H). MS (NH3 -DCI): m/z 673 (M+H, 10%); 617 (M+H--N44, 100 %); 243 (Tr, 20%). Calculated mass for C42H37N6O3 (M+H): 673.292714; found: 673.292470.

Workup

  1. filtrationThe product was filtered through Celite™
  2. washthe cake was washed with ethyl acetate and methylene chloride
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-26227956bd9a476b8e9645e88212d782
Source dataset
uspto-grants-1995_02
Patent number
US05389635

Reaction notes

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