Ammonium Chloride → (E)-tert-butyl 2-(6-benzamidohex-2-enamido)phenylcarbamate

HRID 1776146ノート

反応式

HRID 1776146 の反応式
[C:1]([NH:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[Na].[NH4+].[Cl-]>CO>[C:1]([NH:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]/[C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([NH:9][CH2:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 60207724(E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamateHCID 178418582HCID 178418582、化合物

生成物 2

HCID 60207724(E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate収率 28%HCID 67283444(E)-tert-butyl 2-(6-benzamidohex-2-enamido)phenylcarbamate収率 64%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate (423 mg, 1 mmol) in MeOH was added MeONa (37 mg, 20 mmol), the mixture was stirred for 12 hours. To the reaction mixture was added sat. NH4Cl solution to adjust the pH value to 7-8, then concentrated, the residue was dissolved in DCM, the organic layer was washed with brine, dried over Na2SO4 and concentrated to give the desired compound of (E)-tert-butyl 2-(6-benzamidohex-2-enamido)phenylcarbamate (14) (270 mg, 64%) and (E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamate (15) (123 mg, 28%) as white solids after purification by column chromatography (eluent: DCM:MeOH=100:1). LC-MS found 424 (M+H)+. Analytical data for compound 14: 1H NMR (300 MHz, DMSO): δ 1.504 (s, 9H), 1.791 (m, 2H), 2.308 (m, 2H), 3.465 (m, 2H), 5.988 (d, J=15.6 Hz, 1H), 6.146 (s, 1H), 6.897-6.984 (m, 3H), 7.141-7.165 (m, 2H), 7.418 (s, 1H). 7.515 (s, 1H), 7.4585 (d, 2H). 8.133 (s, 1H).

後処理

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in DCM
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b09a0e82622e472b985bdbf07eaaf448
出典データセット
uspto-grants-2016_02
特許番号
US09265734B2

反応ノート

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