Water → HCID 60133236, compound

HRID 2246617Notes

Reaction equation

HRID 2246617 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.O[N:21]1[C:25]2N=CC=C[C:24]=2N=N1.C(N)C.O>O1CCCC1.C(Cl)(Cl)Cl>[CH2:25]([NH:21][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([B:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]2)[CH:4]=1)[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 181649HOAtHCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 60133236HCID 60133236, compoundYield 831.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.3 g) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.44 g) and 3H-[1,2,3] 1-hydroxy-7-azabenzotriazole (0.077 g) was added to a stirred solution of ethylamine in tetrahydrofuran (2M, 5 ml) in chloroform (30 ml) and the mixture was stirred for 24 h. The mixture was poured into water, passed through a hydrophobic filter tube and the organic phase was concentrated under vacuum. The residual solid was purified on an SCX cartridge eluting with methanol to give the title compound as a pale yellow solid (1.36 g)

Workup

  1. custompassed through a hydrophobic filter tube
  2. concentrationthe organic phase was concentrated under vacuum
  3. customThe residual solid was purified on an SCX cartridge
  4. washeluting with methanol

Sources & evidence

ORD record
ord-fb71dd7233084bef85196385e32813f3
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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