Acetonitrile → HCID 86688950, compound

HRID 404689Notes

Reaction equation

HRID 404689 reaction equation
O.O=[CH:3][C:4]([OH:6])=[O:5].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.[C:21](#[N:23])[CH3:22]>>[N:7]1([CH:3]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)[C:4]([O:6][C@@H:22]2[CH:10]3[CH2:11][CH2:12][N:23]([CH2:8][CH2:9]3)[CH2:21]2)=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 27339602-Thiopheneboronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 86688950HCID 86688950, compound

Procedure

A mixture of 2-oxoacetic acid hydrate (216 mg, 2.34 mmol), piperidine (0.23 ml, 2.34 mmol) and thiophen-2-ylboronic acid (300 mg, 2.34 mmol) in acetonitrile (11.7 ml) was heated to reflux for 2.5 hours. The reaction was cooled at room temperature and the suspension was filtered on a buckner funnel washing with acetonitrile (10 ml). The solid was recovered from the filter giving the title compound (528 mg, quantitative yield) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hours
  3. filtrationthe suspension was filtered on a buckner funnel
  4. washwashing with acetonitrile (10 ml)
  5. customThe solid was recovered from the filter

Sources & evidence

ORD record
ord-6b80333a2ba5460ba41f5f6427bb96af
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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