HOAt → HCID 58828525, compound

HRID 2358293Notes

Reaction equation

HRID 2358293 reaction equation
O[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4](=[O:13])[O:3]1.[CH2:20]([O:22][CH:23]([O:29][CH2:30][CH3:31])[CH2:24][NH:25][CH2:26][C:27]#[N:28])[CH3:21].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[C:2]([C:10]1[CH:9]=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[C:4]([N:25]([CH2:26][C:27]#[N:28])[CH2:24][CH:23]([O:22][CH2:20][CH3:21])[O:29][CH2:30][CH3:31])=[O:13])(=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 181649HOAtHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19094668HCID 19094668, compoundHCID 22555951HCID 22555951, compound

Product 1

HCID 58828525HCID 58828525, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3 (1.00 g, 3.91 mmol), 4 (740 mg, 4.30 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (826 mg, 4.30 mmol), 1-hydroxy-7-azabenzotriazole (585 mg, 4.30 mmol) and NN-diisopropylethylamine (0.748 mL, 4.30 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 2 days. The contents of the reaction flask were poured into water and sat. sodium bicarbonate then extracted with ethyl acetate (3×). The combined organic extracts were washed with 5% potassium bisulfate and brine. The organic layer was dried with sodium sulfate (anh.), filtered and concentrated in vacuo. Flash column chromatography (hexane/ethyl acetate 70:30) gave 5 (1.05 g, 68%)

Workup

  1. extractionthen extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with 5% potassium bisulfate and brine
  3. dry with materialThe organic layer was dried with sodium sulfate (anh.)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75030f3e2a764557aaafaf063071c72d
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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