Sodium Iodide → HCID 18931124、化合物

HRID 1599002ノート

反応式

HRID 1599002 の反応式
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:3]1.Br[CH2:21][CH:22]([OH:25])[CH2:23][OH:24].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH2:21][CH:22]([OH:25])[CH2:23][OH:24])[C:5](=[O:7])[C:4]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[NH:3]1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 208273-Bromo-1,2-propanediol2 回HCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

生成物 1

HCID 18931124HCID 18931124、化合物収率 17.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of tert-butyl 2,4-dioxo-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (6.9 g, 25.6 mmol), 3-bromo-1,2-propanediol (4.4 g, 28 mmol), sodium iodide (1.5 g, 10 mmol), potassium carbonate (14 g) and DMF (25 mL) was stirred approximately 48 hours at 100° C. Additional 3-bromo-1,2-propanediol (1.5 g, 10 mmol) was added, and the stirring and heating continued for an additional 72 hours. After cooling, the mixture was filtered, the solvent removed from the filtrate under vacuum, and the residue was purified by chromatography eluting with ethyl acetate containing 0.5-1% acetic acid. The fractions containing the product were combined and concentrated, and the residue was treated with ethyl acetate to give tert-butyl 2,4-dioxo-3-(2,3-dihydroxypropyl)-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (1.5 g, 4.4 mmol) as a white solid, m.p. 167°-170° C.

後処理

  1. temperaturethe stirring and heating
  2. waitcontinued for an additional 72 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe solvent removed from the filtrate under vacuum
  6. customthe residue was purified by chromatography
  7. washeluting with ethyl acetate containing 0.5-1% acetic acid
  8. additionThe fractions containing the product
  9. concentrationconcentrated
  10. additionthe residue was treated with ethyl acetate

出典と根拠

ORDレコード
ord-b16ae4bca1d4472196a882a508e07e35
出典データセット
uspto-grants-1998_04
特許番号
US05739336

反応ノート

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