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

HRID 1776146Notes

Reaction equation

HRID 1776146 reaction equation
[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

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 60207724(E)-tert-butyl 2-(6-benzamidohex-3-enamido)phenylcarbamateHCID 178418582HCID 178418582, compound

Product 2

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b09a0e82622e472b985bdbf07eaaf448
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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