Dimethylformamide → N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-4-(benzyloxy)pentanamide

HRID 1661394Notes

Reaction equation

HRID 1661394 reaction equation
[CH2:1]([O:8][CH:9]([CH3:15])[CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.Cl.[NH2:28][C:29]1[C:37]([OH:38])=[C:36]2[C:32]([CH2:33][CH2:34][CH:35]2[CH2:39][CH2:40][NH:41][C:42](=[O:44])[CH3:43])=[CH:31][CH:30]=1>O1CCCC1.N1C=CC=CC=1>[C:42]([NH:41][CH2:40][CH2:39][CH:35]1[C:36]2[C:32](=[CH:31][CH:30]=[C:29]([NH:28][C:12](=[O:14])[CH2:11][CH2:10][CH:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH3:15])[C:37]=2[OH:38])[CH2:33][CH2:34]1)(=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 577812604-(Benzyloxy)pentanoic AcidHCID 67354374N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide Hydrochloride

Product 1

HCID 57781273N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-4-(benzyloxy)pentanamideYield 57.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(Benzyloxy)pentanoic acid (230 mg, 1.10 mmol) was dissolved in tetrahydrofuran (10 mL), oxalyl chloride (90 μL, 1.05 mmol) and dimethylformamide (10 μL) were added under ice-cooling, and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure, and the residue was diluted with dichloromethane (1 mL). This was added to a solution of N-[2-(6-amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (244 mg, 0.903 mmol) in pyridine (10 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 min. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0) to give the title compound (220 mg, yield 57%).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was diluted with dichloromethane (1 mL)
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 15 min
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0)

Sources & evidence

ORD record
ord-ea0d2df5a43f45639792ea4489b7f81d
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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