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

HRID 1066038ノート

反応式

HRID 1066038 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 712Formaldehyde溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d40aa16915ea4b7d81bd8b238db3afd4
出典データセット
uspto-grants-2001_06
特許番号
US06242422B1

反応ノート

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