Triethylamine → HCID 23092672, compound

HRID 2235425Notes

Reaction equation

HRID 2235425 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][CH3:12])[NH:7][C:6](=[O:13])[C:5]2([CH3:15])[CH3:14].[C:16]1(/[CH:22]=[CH:23]/[C:24]([OH:26])=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:27]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(CC)CC.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:16]1(/[CH:22]=[CH:23]/[C:24]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][C:10]=2[NH:11][CH3:12])[N:7]([CH3:27])[C:6](=[O:13])[C:5]3([CH3:15])[CH3:14])=[O:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 444539Cinnamic AcidHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 23092640HCID 23092640, compound

Product 1

HCID 23092672HCID 23092672, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of B1 (200 mg) in N,N-dimethylformamide (1.5 ml) is added (E)-3-phenyl-acrylic acid (142 mg; 0.96 mmol), TBTU (308 mg; 0.96 mmol) and NEt3 (97 mg; 0.96 mmol). The mixture is stirred at RT for 20 h. Saturated NaHCO3 solution is added and the aqueous layer is extracted with EtOAc (3×20 ml). The combined organic layer is washed with brine, dried and concentrated in vacuo. The crude material is purified by flash chromatography on silica gel eluting with light petroleum/EtOAc (1:2) to give the compound (288 mg).

Workup

  1. extractionthe aqueous layer is extracted with EtOAc (3×20 ml)
  2. washThe combined organic layer is washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude material is purified by flash chromatography on silica gel eluting with light petroleum/EtOAc (1:2)

Sources & evidence

ORD record
ord-50212aa721dd47f98e774a49b6afb7b8
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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