Diisopropylethylamine → tert-butyl N-[N-[2-(2,6-dimethylphenoxy)acetyl]carbamimidoyl]carbamate

HRID 873775ノート

反応式

HRID 873775 の反応式
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.C([N:17](C(C)C)CC)(C)C.N[N:24]([CH:32]=[NH:33])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].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:17]=[C:32]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[NH:33][C:6](=[O:8])[CH2:5][O:4][C:3]1[C:9]([CH3:13])=[CH:10][CH:11]=[CH:12][C:2]=1[CH3:1]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 101369(2,6-Dimethylphenoxy)acetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 86691067Tert-butyl amino(imino)methylcarbamate

生成物 1

HCID 149434096tert-butyl N-[N-[2-(2,6-dimethylphenoxy)acetyl]carbamimidoyl]carbamate収率 94%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(2,6-Dimethylphenoxy)acetic acid (5.41 g; 30 mmol), diisopropylethylamine (19.39 g; 150 mmol), tert-butyl amino(imino)methylcarbamate (5.73 g; 36 mmol), and 1-hydroxybenzotriazole monohydrate (5.52 g; 36 mmol) were dissolved in N,N-dimethylformamide (120 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (13.66 g; 36 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, 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 crystals were dispersed in diethyl ether, collected by filtration and dried to give 9.03 g of the title compound (yield 94%).

後処理

  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. additionThe resulting crystals were dispersed in diethyl ether
  5. filtrationcollected by filtration
  6. customdried

出典と根拠

ORDレコード
ord-320524c1c0524f128ac0d46c9b25fbe3
出典データセット
uspto-grants-2015_03
特許番号
US08975411B2

反応ノート

読み込み中…