Diisopropylamine → HCID 53944664, compound

HRID 379276Notes

Reaction equation

HRID 379276 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].C[O:22][C:23](=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[CH2:36][CH2:35][CH2:34][NH:33][C:32]=2[N:31]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:17]([O:16][C:13](=[O:15])[CH2:14][C:23](=[O:22])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[CH2:36][CH2:35][CH2:34][NH:33][C:32]=2[N:31]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 516892Sodium BicarbonateHCID 54211117HCID 54211117, compoundHCID 178418339Butyllithium

Product 1

HCID 53944664HCID 53944664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a stirred solution of diisopropylamine (5.17 mL, 36.9 mmol) in anhydrous tetrahydrofuran (100 mL) at −78° C. was added a solution of n-butyllithium in hexanes (16.2 mL of a 2.5 M solution). After 5 minutes, t-butyl acetate (4.97 mL, 36.9 mmol) was added. After an additional 5 minutes, 7-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-heptanoic acid methyl ester 29-4 (3.4 g, 12.3 mmol) in tetrahydrofuran (30 mL) was added and the solution was warmed to −40° C. for one hour. The reaction mixture was then poured into saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with ethyl acetate to give 29-5 as a yellowish oil.

Workup

  1. waitAfter an additional 5 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting oil was purified by flash column chromatography over silica gel with ethyl acetate

Sources & evidence

ORD record
ord-eba4491d42b44b6ca11cae4e31b4c1ba
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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