Phthalamic acid → N'-(1-Carbamoyl-1,2-dimethylpropyl)-N,N-diethyl-3,4-(methylenedioxy)phthalamide

HRID 1646444ノート

反応式

HRID 1646444 の反応式
[C:1]([OH:12])(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([NH2:6])=[O:5].Cl[C:14]([O:16]CC)=[O:15].C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.[CH3:26][C@@:27]([C:32]([NH2:34])=[O:33])([CH:29]([CH3:31])[CH3:30])N>O1CCCC1.O>[C:32]([C:27]([NH:6][C:4](=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[C:8]2[O:16][CH2:14][O:15][C:7]=12)[C:1]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:12])([CH3:26])[CH:29]([CH3:31])[CH3:30])(=[O:33])[NH2:34]

参加物

7

反応物 4

HCID 6957Phthalamic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10154071(S)-2-Amino-2,3-dimethylbutanamide

生成物 1

HCID 54453674N'-(1-Carbamoyl-1,2-dimethylpropyl)-N,N-diethyl-3,4-(methylenedioxy)phthalamide収率 74.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
10 °C

実験手順

A solution of N,N-diethyl-5,6-)methylenedioxy)phthalamic acid (3.00 g, 11.0 mmol) in tetrahydrofuran, under nitrogen at room temperature is treated with ethyl chloroformate (1.10 mL, 11.0 mmol), cooled to 10° C., treated with triethylamine (1.70 mL, 12.0 mmol), stirred for 30 minutes at 10° C., treated dropwise with a solution of α-methylvalinamide (1.43 g, 11.0 mmol) in tetrahydrofuran, stirred overnight at ambient temperatures, treated with water and concentrated in vacuo. The aqueous residue is extracted with ethyl acetate; the extracts are combined, washed with brine and saturated sodium bicarbonate, dried (MgSO4), and concentrated in vacuo to afford the title product as an amber foam 3.10 g (74.7%), identified by NMR and mass spectral analysis.

後処理

  1. stirringstirred overnight at ambient temperatures
  2. concentrationconcentrated in vacuo
  3. extractionThe aqueous residue is extracted with ethyl acetate
  4. washwashed with brine and saturated sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0353ecbbe0dc4ae2a8d79fc0ded84164
出典データセット
uspto-grants-1993_01
特許番号
US05180419

反応ノート

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