Benzylamine → HCID 58556986, compound

HRID 469478Notes

Reaction equation

HRID 469478 reaction equation
[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[C:13]1([CH2:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.O=[CH:23][C:24]([OH:26])=[O:25]>C(#N)C>[S:1]1[CH:5]=[C:4]([CH:23]([NH:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:24]([OH:26])=[O:25])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 2776344(1-Benzothiophen-3-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 58556986HCID 58556986, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of benzo[b]thiophen-3-ylboronic acid (300 mg, 1.68 mmol), phenylmethanamine (184 μl, 1.68 mmol) and 2-oxoacetic acid hydrate (155 mg, 1.68 mmol) in acetonitrile (20 ml) was stirred at room temperature for 2 hours. The solvent was removed and crude was triturated with Et2O/CH3CN (9/1) to obtain 2-(benzo[b]thiophen-3-yl)-2-(benzylamino)acetic acid (303 mg, 60.5% yield).

Workup

  1. customThe solvent was removed
  2. customcrude was triturated with Et2O/CH3CN (9/1)

Sources & evidence

ORD record
ord-dbd72fbb2af145e6aa11022e16828ef0
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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