1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57842615, compound

HRID 735678Notes

Reaction equation

HRID 735678 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][O:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:14]([O:21][C:22](=[O:32])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][CH2:8][C:9]([NH:31][C:27]2[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=2)[CH2:24][NH:23][C:22](=[O:32])[O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 133921((4-Bromobenzyl)oxy)acetic acidHCID 181649HOAtHCID 27573803-N-Cbz-Aminomethylaniline

Product 1

HCID 57842615HCID 57842615, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 67A (245 mg, 1 mmol) and 66A (268 mg, 1.05 mmol) in DMF (4 mL), was added EDCI (288 mg, 1.5 mmol), HOAt (14 mg, 0.1 mmol) and DIEA (0.54 mL, 3 mmol). The mixture was stirred rt for 16 h, then was quenched with water and extracted with EtOAc (3×20 mL). The organic layer washed by brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-40% EtOAc in hexanes) gave 67B (300 mg, 62%). MS (ESI) m/z 483.3 (M+H)+.

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe organic layer washed by brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification via flash chromatography (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ea56fc1f41df49b29f8df13729886954
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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