Diisopropylethylamine → HCID 123681539, compound

HRID 595791

Reaction equation

HRID 595791 reaction equation
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([F:13])[CH:5]=1)([OH:3])[OH:2].[CH3:14][S:15]([C:18]1[CH:19]=[C:20]([CH2:24][NH2:25])[CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:16].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[F:13][C:6]1[CH:5]=[C:4]([B:1]([OH:2])[OH:3])[CH:12]=[CH:11][C:7]=1[C:8](=[O:10])[NH:25][CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:19]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2760937(3-(Methylsulfonyl)phenyl)methanamineHCID 27632014-Carboxy-3-fluorophenylboronic acid

Product 1

HCID 123681539HCID 123681539, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-borono-2-fluorobenzoic acid (218 mg, 1.2 mmol), (3-(methylsulfonyl)phenyl)-methanamine (200 mg, 1.08 mmol), DIEA (0.754 mL, 4.32 mmol) and TBTU (381 mg, 1.2 mmol) in DMF (2 mL) was stirred at room temperature for 2 days, then the reaction mixture was diluted with water (10 mL), and product precipitated out as gum, and the supernatant was separated via centrifugation, and the gummy residue was sonicated with water (3 mL), and the gummy residue was further dried under high vacuum yielding 3-fluoro-4-(3-(methylsulfonyl)benzylcarbamoyl)-phenylboronic acid (335 mg, 88%) as white foam. LCMS (m/z): 352.1 (MH+), 0.51 min.

Workup

  1. customprecipitated out as gum
  2. customthe supernatant was separated via centrifugation
  3. customthe gummy residue was sonicated with water (3 mL)
  4. customthe gummy residue was further dried under high vacuum

Sources & evidence

ORD record
ord-3417773766be496d8412b0b4494e335c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Linked notes

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