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

HRID 1371282ノート

反応式

HRID 1371282 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-f9f3d418cfa242729fd21b2b28cc085a
出典データセット
uspto-grants-2007_01
特許番号
US07157430B2

反応ノート

読み込み中…