1,1'-Carbonyldiimidazole → 2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide

HRID 23201Notes

Reaction equation

HRID 23201 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C:7]([OH:9])=O)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH2:30]([NH2:41])[CH2:31][C:32]1[CH:40]=[CH:39][C:38]2[O:37][CH2:36][O:35][C:34]=2[CH:33]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([CH2:3][CH2:4][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C:7]([NH:41][CH2:30][CH2:31][C:32]1[CH:40]=[CH:39][C:38]2[O:37][CH2:36][O:35][C:34]=2[CH:33]=1)=[O:9])#[N:2]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 74246Phenethylamine, 3,4-methylenedioxy-, hydrochlorideHCID 81531DiisopropylethylamineHCID 224882542-((tert-Butoxycarbonyl)(2-cyanoethyl)amino)acetic acid

Product 1

HCID 224876962-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamideYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the preparation of compounds of formula (Yc3) above, to 2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]acetic acid (8.3 g, 39 mmol) dissolved in CH2Cl2 (100 mL) was added carbonyldiimidazole (6.2 g, 38 mmol). After stirring for 30 minutes, homopiperonylamine, hydrochloride (8.0 g, 41 mmol) and diisopropylethylamine (7.5 mL, 43 mmol) were added. After stirring for 18 hours, most of the solvent was removed in vacuo and the residue was partitioned with ethyl acetate and 1N HCl. The organic layer was separated, washed with aqueous bicarbonate and brine, dried (Na2SO4), and the solvent was removed in vacuo to give 13 g of 2-[(2-cyanoethyl)(dimethylethoxycarbonyl)amino]-N-[2-(1,3-benzodioxol-5-yl)ethyl]acetamide.

Workup

  1. stirringAfter stirring for 18 hours, most of the solvent
  2. customwas removed in vacuo
  3. customthe residue was partitioned with ethyl acetate and 1N HCl
  4. customThe organic layer was separated
  5. washwashed with aqueous bicarbonate and brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-da6aae41aba44abbb64e28fe925774e8
Source dataset
uspto-grants-2005_02
Patent number
US06849739B2

Reaction notes

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