1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53757316, compound

HRID 398791Notes

Reaction equation

HRID 398791 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[NH2:37][CH:38]1[C:44](=[O:45])[NH:43][C:42]2[CH:46]=[CH:47][C:48]3[C:53]([C:41]=2[CH2:40][CH2:39]1)=[CH:52][CH:51]=[CH:50][CH:49]=3>CN(C=O)C.C(OCC)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11](=[O:13])[NH:37][CH:38]1[C:44](=[O:45])[NH:43][C:42]2[CH:46]=[CH:47][C:48]3[C:53]([C:41]=2[CH2:40][CH2:39]1)=[CH:52][CH:51]=[CH:50][CH:49]=3)([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 18968908HCID 18968908, compound

Product 1

HCID 53757316HCID 53757316, compoundYield 103.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-tert-butyloxycarbonylamino-3-methylbutanoic acid (2.43 g, 11.2 mmol) and 1-hydroxybenzotriazole (1.52 g, 11.3 mmol) in DMF (30 ml) was placed under an atmosphere of nitrogen. EDAC (2.19 g, 11.4 mmol) was added and the reaction mixture was stirred for 10 minutes at room temperature. Unresolved 3-amino-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]- azepine (2.3 g, 10.2 mmol) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was poured into water (200 ml) and the solution was extracted with dichloromethane (2×250 ml). The combined organic extracts were washed with 10% sodium bicarbonate (2×150 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give a solid residue which was suspended in diethyl ether. Filtration and drying afforded 4.5 g of (1,1-dimethyl -2-(4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)carbamic acid tert-butyl ester.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionthe solution was extracted with dichloromethane (2×250 ml)
  3. washThe combined organic extracts were washed with 10% sodium bicarbonate (2×150 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customto give a solid residue which
  7. filtrationFiltration
  8. customdrying

Sources & evidence

ORD record
ord-d3eb8e64e2ec430e85c33afd98a4537a
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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