Tetrahydrofuran → HCID 42635717, compound

HRID 1674679Notes

Reaction equation

HRID 1674679 reaction equation
[OH-].[Na+].C(OC([N:10]1[CH2:15][C@@H:14]([CH2:16][O:17][Si](C(C)C)(C(C)C)C(C)C)[C@H:13]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([O:36][CH3:37])=O)=[CH:30][CH:29]=2)[C@@H:12]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]3[O:48][CH2:47][C:46](=O)[N:45]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[C:44]=3[CH:55]=2)[CH2:11]1)=O)(C)(C)C.[CH2:56]1[CH2:60][O:59][CH2:58][CH2:57]1>O>[CH2:60]([O:59][C@H:58]([CH3:57])[CH2:37][O:36][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([C@@H:13]2[C@@H:12]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][C:43]4[O:48][CH2:47][CH2:46][N:45]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[C:44]=4[CH:55]=3)[CH2:11][NH:10][CH2:15][C@H:14]2[CH2:16][OH:17])=[CH:29][CH:30]=1)[CH3:56]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67335432HCID 67335432, compound

Product 1

HCID 42635717HCID 42635717, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4.30 mmol of NaOH are added to a solution of 1.05 mmol of (3R,4R,5S)-4-(4-methoxycarbonyl-phenyl)-3-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-5-triisopropylsilanyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester in 10 ml of THF and 10 ml of H2O. The resulting reaction mixture is stirred at 90° C. for 16 h and then cooled to RT. After dilution with H2O and acidification (pH 3) with 4N aqueous HCl, the mixture is extracted with TBME (2×)—the combined organic phases are washed with brine, dried over Na2SO4 and concentrated by evaporation. The crude title compound is obtained as a viscous brown oil. Rf=0.24 (EtOAc/heptane 2:1+a drop of formic acid); Rt=6.71 (gradient I).

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to RT
  3. extractionAfter dilution with H2O and acidification (pH 3) with 4N aqueous HCl, the mixture is extracted with TBME (2×)—the combined organic phases
  4. washare washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2ef33a5fdbd84b198c6100d5f8e2188c
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

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