Triethylamine → 5-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 1952589Notes

Reaction equation

HRID 1952589 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:16]([OH:18])=O)=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[C:60]([Si:64]([CH3:75])([CH3:74])[O:65][C:66]1[CH:67]=[C:68]([CH:71]=[CH:72][CH:73]=1)[CH2:69][NH2:70])([CH3:63])([CH3:62])[CH3:61]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:16](=[O:18])[NH:70][CH2:69][C:68]2[CH:71]=[CH:72][CH:73]=[C:66]([O:65][Si:64]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:74])[CH3:75])[CH:67]=2)=[CH:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222661693-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenemethanamineHCID 581210855-(Methoxycarbonyl)-4-phenylthiophene-2-carboxylic acid

Product 1

HCID 682269645-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-phenyl-thiophene-2-carboxylic acid methyl esterYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-Phenyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (500 mg, 1.91 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.53 mL, 3.82 mmol), HBTU (1.45 g, 3.82 mmol), HOBT (390 mg, 3.82 mmol), and 3-(tert-Butyl-dimethyl-silanyloxy)-benzylamine (540 mg, 2.29 mmol). The mixture was stirred at room temperature 1 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-30% EtOAc in hexane to afford the desired product (0.36 g, 39% yield).

Workup

  1. customquenched
  2. additionby pouring into EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with 0-30% EtOAc in hexane

Sources & evidence

ORD record
ord-d270c2a0fa4347b0b2c0f74e9a0ffde8
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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