1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57930951, compound

HRID 545214Notes

Reaction equation

HRID 545214 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:23](=[CH:24][CH:25]=1)[O:22][C:9]1([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH2:8][C:7]2=[O:26])([OH:3])=O.Cl.[NH2:28][CH2:29][C:30]([NH2:32])=[O:31].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:30]([CH2:29][NH:28][C:1]([C:4]1[CH:5]=[C:6]2[C:23](=[CH:24][CH:25]=1)[O:22][C:9]1([CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:13][CH2:14]1)[CH2:8][C:7]2=[O:26])=[O:3])(=[O:31])[NH2:32]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723639Glycinamide hydrochlorideHCID 509991921'-(tert-Butoxycarbonyl)-4-oxo-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]-6-carboxylic acid

Product 1

HCID 57930951HCID 57930951, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-butyl 6-carboxy-4-oxospiro(chroman-2,4′-piperidine)-1′carboxylate (7.50 g, 20.8 mmol), glycinamide hydrochloride (2.76 g, 24.9 mmol), EDCI (4.78 g, 24.9 mmol), HOBT (3.78 g, 24.9 mmol), and TEA (5.80 ml, 41.6 mmol) were suspended in DMF (75 ml) and stirred at room temperature for 23 h. After removal of the solvent, the residue was diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with saturated NaHCO3 aq. and brine, dried over MgSO4. The desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was triturated with MeOH-Et2O and the insoluble solid was collected through filtration to obtain the intended compound as a colorless solid.

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with EtOAc and H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layer was washed with saturated NaHCO3 aq. and brine
  5. dry with materialdried over MgSO4
  6. customThe desiccant was removed through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was triturated with MeOH-Et2O
  9. filtrationthe insoluble solid was collected through filtration

Sources & evidence

ORD record
ord-5aac4dfe5c7148b0ab26d4de609b21f7
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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