Diisopropylethylamine → tert-butyl N-[N-[3-(2,4,6-trimethylphenyl)propanoyl]carbamimidoyl]carbamate

HRID 873781노트

반응식

HRID 873781 반응식
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][CH2:10][C:11]([OH:13])=O.C([N:18](C(C)C)CC)(C)C.N[N:25]([CH:33]=[NH:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[NH:18]=[C:33]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[NH:34][C:11](=[O:13])[CH2:10][CH2:9][C:2]1[C:1]([CH3:14])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 2325363-(2,4,6-Trimethylphenyl)propanoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 86691067Tert-butyl amino(imino)methylcarbamate

생성물 1

HCID 149434104tert-butyl N-[N-[3-(2,4,6-trimethylphenyl)propanoyl]carbamimidoyl]carbamate수율 93%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-Mesitylpropionic acid (4.40 g; 23 mmol), diisopropylethylamine (14.8 g; 115 mmol), tert-butyl amino(imino)methylcarbamate (4.40 g; 28 mmol), and 1-hydroxybenzotriazole monohydrate (4.22 g; 28 mmol) were dissolved in N,N-dimethylformamide (92 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (10.5 g; 28 mmol) was added thereto, and the mixture was stirred for 17 hours at room temperature. To the reaction solution, ethyl acetate (300 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution, and then brine. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure. The resulting oily substance was crystallized from diethyl ether/diisopropyl ether, collected by filtration and dried to give 7.10 g of the title compound (yield 93%).

후처리

  1. washthe mixture was washed with 10% aqueous citric acid solution, brine, saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customThe resulting oily substance was crystallized from diethyl ether/diisopropyl ether
  5. filtrationcollected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-7d97125c53b141c69e8201dc366f5e1c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975411B2

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