Ammonia → [2-(2-carbamoyl-benzo[1,3]dioxol-5-yl)-1-methyl-ethyl]-ethyl-carbamic Acid Tert-Butyl Ester

HRID 2099712Notes

Reaction equation

HRID 2099712 reaction equation
C([O:3][C:4]([CH:6]1[O:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][CH:16]([N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH3:20])[CH3:17])=[CH:14][C:8]=2[O:7]1)=O)C.[NH3:28]>CO>[C:24]([O:23][C:21](=[O:22])[N:18]([CH:16]([CH3:17])[CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[O:10][CH:6]([C:4](=[O:3])[NH2:28])[O:7][C:8]=2[CH:14]=1)[CH2:19][CH3:20])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 689000045-[2-(tert-butoxycarbonyl-ethyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic Acid Ethyl Ester

Product 1

HCID 68896083[2-(2-carbamoyl-benzo[1,3]dioxol-5-yl)-1-methyl-ethyl]-ethyl-carbamic Acid Tert-Butyl EsterYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.04 g (5.37 mmol) of 2D was added 30 mL of anhydrous methanol, and ammonia gas was passed through the solution for 1 hour at room temperature. The mixture was concentrated to dryness and the residue purified by silica gel column chromatography using 30% hexane in ethyl acetate to give 1.8 g (5.13 mmol, 96%) of 2E as a colorless gum (M+Na, 373).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f30fcc67d6514843bbfec1fdc59cf301
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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