Potassium Carbonate → HCID 68922176, compound

HRID 1804687Notes

Reaction equation

HRID 1804687 reaction equation
Cl[CH2:2][O:3][C:4](=[O:15])[CH:5]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:6].[CH2:16]([N:18]1[C:23]([C:24]([C:26]2[CH:27]=[C:28]([CH:31]=[C:32]([CH3:34])[CH:33]=2)[C:29]#[N:30])=[O:25])=[C:22]([CH:35]([CH3:37])[CH3:36])[C:21](=[O:38])[NH:20][C:19]1=[O:39])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:29]([C:28]1[CH:27]=[C:26]([CH:33]=[C:32]([CH3:34])[CH:31]=1)[C:24]([C:23]1[N:18]([CH2:16][CH3:17])[C:19](=[O:39])[N:20]([CH2:2][O:3][C:4](=[O:15])[CH:5]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:6])[C:21](=[O:38])[C:22]=1[CH:35]([CH3:37])[CH3:36])=[O:25])#[N:30]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 25215428AinuovirineHCID 72978647HCID 72978647, compound

Product 1

HCID 68922176HCID 68922176, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butoxycarbonylamino-propionic acid chloromethyl ester (4) (0.6207 g, 2.61 mmol) and 3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (0.780 g, 2.40 mmol) in DMF (10 mL) was added K2CO3 and tetrabutylammonium iodide (0.193 g, 0.522 mmol), and the reaction mixture stirred for 48 h. The reaction mixture was concentrated, diluted with ethyl acetate and washed with H2O (2×), brine, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexane) to give a yellow foam (5) (0.9028 g, 71%). 1H NMR (300 MHz, CDCl3): 8.01 (s, 1H), 7.94 (s, 1H), 7.77 (s, 1H), 6.1-5.9 (m, 2H), 5.05 (br s, 1H), 4.32 (br s, 1H), 3.9-3.8 (m, 1H), 3.2-3.1 (m, 1H), 2.49 (s, 3H), 2.2-2.1 (m, 1H), 1.39 (s, 9H), 1.37 (s, 3H), 1.2-1.1 (m, 9H). Mass spectrum: 549.1 (M+Na).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with H2O (2×), brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ce583a7fbb2e4b34aa9a791b23c7c778
Source dataset
uspto-grants-2013_01
Patent number
US08354421B2

Reaction notes

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