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

HRID 873776ノート

反応式

HRID 873776 の反応式
[C:1]1([CH3:15])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:9][C@H:10]([CH3:14])[C:11]([OH:13])=O.C([N:19](C(C)C)CC)(C)C.N[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>[NH:19]=[C:34]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[NH:35][C:11](=[O:13])[C@H:10]([O:9][C:2]1[C:1]([CH3:15])=[CH:6][C:5]([CH3:7])=[CH:4][C:3]=1[CH3:8])[CH3:14]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrateHCID 40618694(2R)-2-(Mesityloxy)propionic acidHCID 86691067Tert-butyl amino(imino)methylcarbamate

生成物 1

HCID 149434101tert-butyl N-[N-[(2R)-2-(2,4,6-trimethylphenoxy)propanoyl]carbamimidoyl]carbamate収率 73.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(2R)-2-(Mesityloxy)propionic acid (11.6 g; 55 mmol), diisopropylethylamine (35.6 g; 275 mmol), tert-butyl amino(imino)methylcarbamate (8.8 g; 55 mmol), and 1-hydroxybenzotriazole monohydrate (8.4 g; 55 mmol) were dissolved in N,N-dimethylformamide (150 mL), 2-(1H)-benzotriazol-1-yl-1,1,3,3-tetramethyluronium hexafluorophosphate (20.9 g; 55 mmol) was added thereto, and the mixture was stirred for 18 hours at room temperature. To the reaction solution, ethyl acetate (400 mL) was added, and the mixture was washed sequentially 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 oily substance was crystallized from diisopropyl ether, collected by filtration and dried to give 14.1 g of the title compound (yield 73%).

後処理

  1. washthe mixture was washed sequentially 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. customThe resulting oily substance was crystallized from diisopropyl ether
  5. filtrationcollected by filtration
  6. customdried

出典と根拠

ORDレコード
ord-10b446e757fe49edaf9a6fbb2f690aef
出典データセット
uspto-grants-2015_03
特許番号
US08975411B2

反応ノート

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