Ethyl Acetate → HCID 15222071, compound

HRID 274816Notes

Reaction equation

HRID 274816 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:51][CH2:52][CH3:53])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:9]=1[C:10]([O:12][CH3:13])=[O:11])=O.CC(C[AlH]CC(C)C)C.C(OCC)(=O)C.[NH4+].[Cl-]>C1COCC1>[CH3:13][O:12][C:10]([C:9]1[N:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:7]([CH2:51][CH2:52][CH3:53])=[N:6][C:5]=1[CH2:3][OH:2])=[O:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 15222104HCID 15222104, compound

Product 1

HCID 15222071HCID 15222071, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

To a solution of 7.03 g (10.0 mmole) of 4,5-bis (methoxycarbonyl)-2-propyl-1-[(2'-(N-trityltetrazol-5-yl)biphen-4-yl)methyl]-imidazole in 80 mL anhydrous THF was added 20.0 mL 1.0 M DIBAL-H (20.0 mmole, in THF) at -75° C. The mixture was stirred at -75° C. for 2.5 hours and then warmed to room temperature. After stirring overnight at room temperature, TLC (ethyl acetate) showed no starting material. The mixture was poured into 100 mL saturated aqueous NH4Cl solution and stirred for 20 min.; the product was extracted with 4×200 mL ethyl acetate, and the combined organic layer was washed with brine, dried over MgSO4, and filtered. Solvents were then removed under reduced pressure to yield 6.30 g (89.4%) of the title compound as a white foam. 1H NMR (300 MHz, DMSO-d6): δ 0.77 (t, J=7.3 Hz, 3H); 1.55 (m, 2H); 2.44 (t, J=7.7 Hz, 3H); 3.66 (s, 3H); 4.59 (d, J=6.2 Hz, 2H); 4.82 (t, J=6.2 Hz, 1H); 5.49 (s, 2H); 6.80-7.80 (m, 23H). MS (NH3 -CI/DDIP): m/z 675 (M+H, 26%); 619 (M+H-N4, 100%); 243 (Tr, 19%). Calculated mass for C42H39N6O3 (M+H): 675.308365; found: 675.308581.

Workup

  1. temperaturewarmed to room temperature
  2. stirringAfter stirring overnight at room temperature
  3. stirringstirred for 20 min.
  4. extractionthe product was extracted with 4×200 mL ethyl acetate
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customSolvents were then removed under reduced pressure

Sources & evidence

ORD record
ord-748556b2ae604268ac111334e3ed708e
Source dataset
uspto-grants-1995_02
Patent number
US05389635

Reaction notes

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