Sulfuric Acid → HCID 10374648, compound

HRID 2079465Notes

Reaction equation

HRID 2079465 reaction equation
NC(=O)[C@@H](N[C:6]([C@@H:8]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:9]1)=[O:7])C.[OH:17]S(O)(=O)=O>O1CCOCC1>[C@@H:8]1([C:6]([OH:7])=[O:17])[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:9]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 11401845HCID 11401845, compound

Product 1

HCID 10374648HCID 10374648, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product from Example 4 (25.0 0.112 mol, 97% diastereomeric excess), 1,4-dioxane (50 mL), and 4M H2SO4 (100 mL) were refluxed for 8 hours. The resulting solution was extracted with heptane (3×150 mL). The combined organic extracts were concentrated to afford the title compound (97% enantiomeric excess). The enantiomeric excess of the carboxylic acid was determined by chiral gas chromatography (GC) performed on a Hewlett-Packard 5890 Series gas chromatograph with a flame ionization detector (250° C.), and split mode capillary injection system (ratio 30:1), using a Chiraldex GTA column (30 m×0.25 mm, lot 06847 Serial # G0112-15); 1.0 μL injection volume, 250° C. injection temperature, helium carrier gas at 20 psi, oven temperature 160° C. isothermal, retention time of 9.02 minutes.

Workup

  1. extractionThe resulting solution was extracted with heptane (3×150 mL)
  2. concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-f48a6c67373b4acda4ca33dbf9ec7cba
Source dataset
uspto-grants-2011_04
Patent number
US07932245B2

Reaction notes

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