1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68709601、化合物

HRID 1927796ノート

反応式

HRID 1927796 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21].O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]([CH2:9][C:10]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21])=[O:12])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochlorideHCID 23033833N-(tert-Butoxycarbonyl)-N-(2-methylpropyl)glycine

生成物 1

HCID 68709601HCID 68709601、化合物収率 65%

試薬・触媒・溶媒 2

HCID 8471Triethylamine溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Nα-(tert-Butyloxycarbonyl)-Nα-(2-methylpropyl) glycine (360 mg, 1.56 mmol) was dissolved in CH2Cl2/DMF (9:1, 20 ml). The solution was cooled to 0° C., L-prolinamide hydrochloride (282 mg, 1.87 mmol), 1-hydroxybenzotriazole hydrate (295 mg, 2.18 mmol) and water soluble carbodiimide (358 mg, 1.87 mmol) were added and after 15 min the pH adjusted to pH9 with triethylamine. After 18 h at 0° C. to room temperature the solvent was removed in vacuo and the residue was taken up in ethyl acetate (100 ml). This solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (eluant: 4% methanol, 94% chloroform, 2% triethylamine) to give a colourless oil identified as the title compound (330 mg, 1.01 mmol, 65%).

後処理

  1. customAfter 18 h at 0° C. to room temperature the solvent was removed in vacuo
  2. washThis solution was washed with 0.3M KHSO4, sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (eluant: 4% methanol, 94% chloroform, 2% triethylamine)
  6. customto give a colourless oil

出典と根拠

ORDレコード
ord-5f091af6728144d296ecc31a6dc7dfd2
出典データセット
uspto-grants-2012_05
特許番号
US08183280B2

反応ノート

読み込み中…