(+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedione → (+/-)-1-[3-[[(2,3-Dihydro-1,4-dioxino-[2,3-b]pyridin-3-yl)methyl](phenylmethyl)amino]-2-hydroxypropyl]-2,4-imidazolidine-dione

HRID 30092

反応式

HRID 30092 の反応式
[C:1]1([CH2:7][NH:8][CH2:9][CH:10]2[O:19][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[O:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:20]1[CH2:22][CH:21]1[CH2:23][N:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30]>CO>[O:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[O:19][CH:10]([CH2:9][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:22][CH:21]([OH:20])[CH2:23][N:24]2[CH2:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])[CH2:11]1

参加物

4

反応物 2

HCID 22020929(+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedioneHCID 220209302,3-dihydro-N-(phenylmethyl)-1,4-dioxino[2,3-b]pyridine-3-methanamine

生成物 1

HCID 22020928(+/-)-1-[3-[[(2,3-Dihydro-1,4-dioxino-[2,3-b]pyridin-3-yl)methyl](phenylmethyl)amino]-2-hydroxypropyl]-2,4-imidazolidine-dione収率 62.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 2,3-dihydro-N-(phenylmethyl)-1,4-dioxino[2,3-b]pyridine-3-methanamine (0.0059 mol) and intermediate (18) (0.00497 mol) in methanol (30 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/2-propanone 96/4, 90/10 and 80/20), then CH2Cl2/CH3OH 96/4 and 90/10). The product fractions were collected and the solvent was evaporated, yielding 1.29 g of (±)-1-[3-[[(2,3-dihydro-1,4-dioxino-[2,3-b]pyridin-3-yl)methyl](phenylmethyl)amino]-2-hydroxypropyl]-2,4-imidazolidine-dione (compound 12).

後処理

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/2-propanone 96/4, 90/10 and 80/20)
  4. customThe product fractions were collected
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-0eef55918a5646fd87a8980242071fb0
出典データセット
uspto-grants-2008_09
特許番号
US07423048B2

関連ノート

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