Potassium Carbonate → 2-[(R)-1-(3-Phthalimido-2-oxo-propylamino)-2-methyl-propyl)-3-benzyl-7-chloro-chromen-4-one

HRID 473045Notes

Reaction equation

HRID 473045 reaction equation
[NH2:1][C@@H:2]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:23])[C:15]=1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:12][CH:11]=[C:10]([Cl:24])[CH:9]=2)[CH:3]([CH3:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33](=[O:46])[CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45]>CN(C=O)C>[C:36]1(=[O:45])[N:35]([CH2:34][C:33](=[O:46])[CH2:32][NH:1][C@@H:2]([C:6]2[O:7][C:8]3[C:13]([C:14](=[O:23])[C:15]=2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=[C:10]([Cl:24])[CH:9]=3)[CH:3]([CH3:4])[CH3:5])[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 66755941(R)-2-(1-Amino-2-methylpropyl)-3-benzyl-7-chloro-4H-chromen-4-one

Product 1

HCID 667559422-[(R)-1-(3-Phthalimido-2-oxo-propylamino)-2-methyl-propyl)-3-benzyl-7-chloro-chromen-4-oneYield 108%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-((R)-1-amino-2-methyl-propyl)-3-benzyl-7-chloro-chromen-4-one (0.5 g, 1.5 mMol) and K2CO3 (0.21 g, 1.5 mMol) in DMF (10 mL) was added N-(3-bromo-2-oxopropyl)-phthalimide (0.45 g, 1.5 mMol) (Nair et al.; J. Org. Chem.; 40; 1975; 1745). The reaction was stirred at RT for 3 h, concentrated under vacuum, taken up in EtOAc, washed with water, brine, dried (Na2SO4) and evaporated to give the title compound (0.88 g, 100%) as a yellow solid: MS (ES) m/e 543.2 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-e97479ce5d16403680d2bb8ced1291fd
Source dataset
uspto-grants-2014_01
Patent number
US08633236B2

Reaction notes

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