Phenylboronic Acid → HCID 58557000, compound

HRID 469453Notes

Reaction equation

HRID 469453 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]([O:18][CH3:19])=[O:17].O.O=[CH:22][C:23]([OH:25])=[O:24]>C(#N)C>[CH3:19][O:18][C:16]([C:12]1[S:13][CH:14]=[CH:15][C:11]=1[NH:10][CH:22]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:23]([OH:25])=[O:24])=[O:17]

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58557000HCID 58557000, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of phenylboronic acid (286 mg, 2.35 mmol), methyl 3-aminothiophene-2-carboxylate (369 mg, 2.35 mmol), and 2-oxoacetic acid hydrate (216 mg, 2.35 mmol) in acetonitrile (20 ml) was stirred at room temperature for 2 hours. The reaction was filtered, and the precipitated was washed with little acetonitrile. The solution was concentrated under reduced pressure, and the precipitate was collected again by filtration, washing with little acetonitrile. The combined precipitates were dried under vacuum overnight to obtain 2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetic acid (558 mg, 82% yield).

Workup

  1. filtrationThe reaction was filtered
  2. washthe precipitated was washed with little acetonitrile
  3. concentrationThe solution was concentrated under reduced pressure
  4. filtrationthe precipitate was collected again by filtration
  5. washwashing with little acetonitrile
  6. customThe combined precipitates
  7. customwere dried under vacuum overnight

Sources & evidence

ORD record
ord-4ac5e791d35f477e9179ddd7d73f9299
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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