Diisopropylethylamine → HCID 59497561, compound

HRID 1747378Notes

Reaction equation

HRID 1747378 reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9](F)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:19]([O:21][C:22](=[O:26])[CH2:23][CH2:24][NH2:25])[CH3:20].CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([NH:25][CH2:24][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:26])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 10444351TERT-BUTYL 3-FLUORO-4-NITROBENZOATE

Product 1

HCID 59497561HCID 59497561, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-fluoro-4-nitro-benzoic acid tert-butyl ester (1 g, 4.14 mmol) and Beta-Alanine ethyl ester hydrochloride 1.037 g, 6.75 mmol) were dissolved in DMF (10 ml). To the solution DIEA 0.872 g, 6.75 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was diluted with water (100 ml), extracted with Ethyl acetate 3×, dried over MgSO4, filtered and evaporated to dryness to afford 1.2 g of solid was obtained (86%).

Workup

  1. extractionextracted with Ethyl acetate 3×
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-623d679ffec8480fabab4f5892289edf
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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