HOAt → HCID 20768295, compound

HRID 985157Notes

Reaction equation

HRID 985157 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.[C:20]([O:24][C:25](=[O:33])[NH:26][CH2:27][CH2:28][NH:29][CH2:30][C:31]#[N:32])([CH3:23])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[C:20]([O:24][C:25](=[O:33])[NH:26][CH2:27][CH2:28][N:29]([CH2:30][C:31]#[N:32])[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][C:10]=1[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:3])=[O:13])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 5

HCID 181649HOAtHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20768298HCID 20768298, compoundHCID 22555951HCID 22555951, compound

Product 1

HCID 20768295HCID 20768295, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 110 (2.55 g, 9.96 mmol), 111 (2.38 g, 12.0 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.30 g, 12.0 mmol), 1-hydroxy-7-azabenzotriazole (1.63 g, 12.0 mmol) in N,N-dimethylformamide was stirred at room temperature for 4 days. The contents of the reaction flask were poured into water and sat. sodium bicarbonate. Extracted with methylene chloride (3×). The combined organic extracts were dried with sodium sulfate (anh.) and filtered. Concentration of the filtrate in vacuo followed flash column chromatography (hexane:ethyl acetate 60:40) gave 112 as a white foam (3.16 g, 7.23 mmol, 72.6%).

Workup

  1. extractionExtracted with methylene chloride (3×)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate (anh.)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c8b93727a95047deb0ade3b37eb97cd4
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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