Sulfuric Acid → 5699-79-6

HRID 1534890Notes

Reaction equation

HRID 1534890 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O>O1CCCC1.[OH-].[Na+]>[C:9]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6287L-ValineHCID 7412Benzoyl chloride

Product 1

HCID 7302905699-79-6Yield 111.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of valine (20 g, 0.17 mole) in tetrahydrofuran (20 ml) and 2N NaOH (111 ml) was cooled down to 10° (ice-water bath) under nitrogen and treated dropwise with benzoyl chloride (23.8 ml, 0.21 mole). The reaction mixture was warmed up to room temperature, stirred for 3.0 hours then cooled back down to 0° (ice-salt bath) and treated with concentrated sulfuric acid (8.0 ml). The mixture was extracted with ethyl acetate (3×200 ml). The combined organic extracts were washed with water (100 ml), brine (50 ml), dried (anhydrous MgSO4), filtered and evaporated to dryness to give title compound as a solid (41.97 g, 100% crude yield).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×200 ml)
  2. washThe combined organic extracts were washed with water (100 ml), brine (50 ml)
  3. dry with materialdried (anhydrous MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a7800328aae143caac1ae2d8919f8fb7
Source dataset
uspto-grants-1992_02
Patent number
US05091378

Reaction notes

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