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

HRID 1646444

반응식

HRID 1646444 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0353ecbbe0dc4ae2a8d79fc0ded84164
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180419

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