1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22721236, compound

HRID 1582396Notes

Reaction equation

HRID 1582396 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][C:13]([OH:15])=O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[CH:16]12[N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:20]([CH2:21][CH2:22]1)[CH2:19][NH:18][CH2:17]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O>[O:11]=[C:10]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7](=[O:8])[N:9]1[CH2:12][C:13]([N:18]1[CH2:17][CH:16]2[N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:20]([CH2:21][CH2:22]2)[CH2:19]1)=[O:15]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 20825N-PhthaloylglycineHCID 757711-HydroxybenzotriazoleHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 22721236HCID 22721236, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-phthaloylglycine (725 mg, 3.53 mmol) and tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (500 mg, 2.36 mmol) in CH2Cl2 (20 mL) were added HOBt (481 mg, 3.53 mmol) and WSC (677 mg, 3.53 mmol) at room temperature and the mixture was stirred overnight. To the mixture was added H2O (5 mL) and the organic layer was separated, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (SiO2, 230-400 mesh, 309, CH2Cl2-MeOH=98/2 to 92/8) afforded the product as a white solid (713 mg, 81%).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fc0c18264a545fa824d4495a2af2830
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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