Acetic Acid → HCID 25142339, compound

HRID 1920755Notes

Reaction equation

HRID 1920755 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[C:7]1([C@@H:13]([NH:16][C:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[N:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]=2[CH2:36]Br)=[O:18])[CH2:14][CH3:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)C>O1CCCC1>[C:7]1([C@@H:13]([NH:16][C:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[N:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]=2[CH2:36][N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])=[O:18])[CH2:14][CH3:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 120252-PyrrolidoneHCID 57733278HCID 57733278, compound

Product 1

HCID 25142339HCID 25142339, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-pyrrolidinone (0.1 ml) in tetrahydrofurane (2 ml) sodium hydride (20 mg, 60% dispersion in mineral oil) was added. The reaction mixture was stirred at ambient temperature until the gas evolution ceased then 3-bromomethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (30 mg) was added. After 30 min acetic acid (0.05 ml) was added and volatiles were removed in vacuo. The product was purified by flash chromatography on SiO2 (5 g, 1,2-dichloroethane then gradient 50% to 100% ethyl acetate in heptane) to give 17 mg of white solid. Yield 56%. LC-MS (m/z) 480.5 (MH+); tR=1.21.

Workup

  1. customvolatiles were removed in vacuo
  2. customThe product was purified by flash chromatography on SiO2 (5 g, 1,2-dichloroethane

Sources & evidence

ORD record
ord-9436dbc2075548558a87b2ed7f28f472
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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