Water → HCID 22730418, compound

HRID 2356019Notes

Reaction equation

HRID 2356019 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=O)[CH2:14][S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]12([CH2:11][NH:12][CH2:13][CH2:14][S:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22730197HCID 22730197, compound

Product 1

HCID 22730418HCID 22730418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 68A in THF (5 mL) was treated with 1M LAH in THF (20 mL, 20.0 mmol), heated to reflux, stirred for 24 hours, cooled to room temperature, treated sequentially with water (0.8 mL), 15% NaOH (0.8 mL), and water (2.4 mL), stirred for 30 minutes, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-100% ethyl acetate/hexanes to provide the desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. stirringstirred for 30 minutes
  4. filtrationfiltered through diatomaceous earth (Celite®)
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 20-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bb84a39ad36b4fc3aa5f7452e77456b5
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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