2-(6-Methoxy-2-naphthyl)propionic acid → HCID 18973230、化合物

HRID 975179

反応式

HRID 975179 の反応式
[CH3:1][NH:2][CH2:3][C@H:4]([OH:13])[C:5]1[CH:6]=[CH:7][C:8]([OH:12])=[C:9]([OH:11])[CH:10]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:37][O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[CH:45]=[C:44]([CH:49]([CH3:53])[C:50]([OH:52])=O)[CH:43]=[CH:42]2>C(#N)C>[OH:11][C:9]1[CH:10]=[C:5]([CH:4]([OH:13])[CH2:3][N:2]([CH3:1])[C:50](=[O:52])[CH:49]([C:44]2[CH:43]=[CH:42][C:41]3[C:46](=[CH:47][CH:48]=[C:39]([O:38][CH3:37])[CH:40]=3)[CH:45]=2)[CH3:53])[CH:6]=[CH:7][C:8]=1[OH:12]

参加物

6

反応物 4

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidHCID 5816EpinephrineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 18973230HCID 18973230、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Epinephrine (Aldrich, 3.18 grams [g], 17.3 millimoles [mmol]), 1-hydroxylbenzotriazole hydrate (Aldrich, 1.76 g, 12.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (Aldrich, 2.49 g, 12.9 mmol) were added to acetonitrile (200 milliliters [ml]). After stirring for 10 minutes, a solution of 6-methoxy-α-methyl-2-naphthaleneacetic acid (Aldrich, 2.0 g, 8.66 mmol), in 50 ml of acetonitrile, was added dropwise. After stirring for 16 hours, the reaction mixture was concentrated in vacuo (under reduced pressure), and the residue was partitioned between water (100 ml) and methylene chloride (100 ml). The layers were separated and the aqueous layer was extracted with methylene chloride (2×50 ml) and ethyl acetate (50 ml). The combined organic extracts were treated with methanol until a clear solution was formed. This solution was dried (magnesium sulfate) and concentrated in vacuo. Flash chromatography of the residue (silica gel, 95:5, volume:volume [v:v], methylene chloride:methanol), and concentration of the appropriate fractions resulted in the formation of a solid. The solid was recrystallized from a mixture of ethyl acetate and hexane to give N-(2(3,4-dihydroxyphenyl)-2-hydroxyethyl)-N-methyl-2-(6-methoxy-2-naphthyl)propionamide, a mixture of diastereomers, as a white solid (0.95 g, 27% yield).

後処理

  1. stirringAfter stirring for 16 hours
  2. concentrationthe reaction mixture was concentrated in vacuo (under reduced pressure)
  3. customthe residue was partitioned between water (100 ml) and methylene chloride (100 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with methylene chloride (2×50 ml) and ethyl acetate (50 ml)
  6. additionThe combined organic extracts were treated with methanol until a clear solution
  7. customwas formed
  8. dry with materialThis solution was dried (magnesium sulfate)
  9. concentrationconcentrated in vacuo
  10. customFlash chromatography of the residue (silica gel, 95:5, volume:volume [v:v], methylene chloride:methanol), and concentration of the appropriate fractions resulted in the formation of a solid
  11. customThe solid was recrystallized from a mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-225cc72976a048ff9a2f99ac99079e35
出典データセット
uspto-grants-1997_03
特許番号
US05607966

関連ノート

読み込み中…