Acetic Acid → (S)-3-{(S)-4-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-pentanoylamino}-4-oxo-butyric acid

HRID 1066038Notes

Reaction equation

HRID 1066038 reaction equation
[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([CH:33]=[O:34])[CH2:25][C:26](=NNC(N)=O)[OH:27])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(=[O:37])C.CO>C=O.O>[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([CH:33]=[O:34])[CH2:25][C:26]([OH:27])=[O:37])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 178446027(3 S)-3-[N-((1-naphthyloxy)acetyl)leucinyl]amino-4-oxobutanoic acid semicarbazone

Product 1

HCID 9823074(S)-3-{(S)-4-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-pentanoylamino}-4-oxo-butyric acidYield 79%

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 962WaterSolvent

Procedure

A solution of (3S)-3-[N-((1-naphthyloxy)acetyl)leucinyl]amino-4-oxobutanoic acid semicarbazone (0.320 g, 0.68 mmol) in 37% aqueous formaldehyde(1.0 mL)-acetic acid(1.0 mL)-methanol(3.0 mL) was stirred at room temperature under nitrogen for 3.5 hrs. The resulting solution was diluted with water and extracted with EtOAc. The extract was washed with water and saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was taken up in EtOAc, filtered through Celite and evaporated to dryness. The product was taken up in a small amount of dioxane, diluted with water, frozen and lyophilized to give the title compound (0.222 g, 79%) as a fluffy white solid. TLC(EtOAc-pyridine-AcOH—H2O; 60:20:5:10) Rf=0.65.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with water and saturated NaCl solution
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated to dryness
  5. filtrationfiltered through Celite
  6. customevaporated to dryness
  7. additiondiluted with water
  8. temperaturefrozen

Sources & evidence

ORD record
ord-d40aa16915ea4b7d81bd8b238db3afd4
Source dataset
uspto-grants-2001_06
Patent number
US06242422B1

Reaction notes

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