Diisopropylethylamine → Tert-butyl({[mesityl(methyl)amino]acetyl}amino)(imino)methylcarbamate

HRID 873780노트

반응식

HRID 873780 반응식
[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9]([CH2:11][C:12]([OH:14])=O)[CH3:10].C(N(C(C)C)CC)(C)C.[NH2:25][N:26]([CH:34]=[NH:35])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].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>[C:29]([O:28][C:27](=[O:33])[N:26]([NH:25][C:12](=[O:14])[CH2:11][N:9]([C:2]1[C:1]([CH3:15])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8])[CH3:10])[CH:34]=[NH:35])([CH3:32])([CH3:30])[CH3:31]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 82113003[Mesityl(methyl)amino]acetic acidHCID 86691067Tert-butyl amino(imino)methylcarbamate

생성물 1

HCID 86691074Tert-butyl({[mesityl(methyl)amino]acetyl}amino)(imino)methylcarbamate수율 52.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

[Mesityl(methyl)amino]acetic acid (6.67 g; 32 mmol), diisopropylethylamine (20.68 g; 160 mmol), tert-butyl amino(imino)methylcarbamate (6.11 g; 38 mmol), and 1-hydroxybenzotriazole monohydrate (5.88 g; 38 mmol) were dissolved in N,N-dimethylformamide (150 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (14.56 g; 38 mmol) was added thereto, and the mixture was stirred for 65 hours at room temperature. To the reaction solution, ethyl acetate (400 mL) was added, and the mixture was washed with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure. The resulting crystals were dispersed in diethyl ether, collected by filtration and dried to give 5.82 g of the title compound (yield 52%).

후처리

  1. washthe mixture was washed with 10% aqueous citric acid solution, brine, and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. additionThe resulting crystals were dispersed in diethyl ether
  5. filtrationcollected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-df76d8704cd34a7b8a2a3944fba0c383
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975411B2

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