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

HRID 1952597Notes

Reaction equation

HRID 1952597 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([OH:13])=O)=[CH:8][C:9]=1[Cl:10])=[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:55]([Si:59]([CH3:70])([CH3:69])[O:60][C:61]1[CH:62]=[C:63]([CH:66]=[CH:67][CH:68]=1)[CH2:64][NH2:65])([CH3:58])([CH3:57])[CH3:56]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:13])[NH:65][CH2:64][C:63]2[CH:66]=[CH:67][CH:68]=[C:61]([O:60][Si:59]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:69])[CH3:70])[CH:62]=2)=[CH:8][C:9]=1[Cl:10])=[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 682266273-Chloro-thiophene-2,5-dicarboxylic acid 2-methyl ester

Product 1

HCID 682270485-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-chloro-thiophene-2-carboxylic acid methyl esterYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-Chloro-thiophene-2,5-dicarboxylic acid 2-methyl ester (500 mg, 2.27 mmol) in anhydrous DMF (10 mL) was added triethylamine (1.0 mL, 6.81 mmol), HBTU (1.03 g, 2.72 mmol), HOBT (370 mg, 2.72 mmol), and 3-(tert-Butyl-dimethyl-silanyloxy)-benzylamine (650 mg, 2.72 mmol). The mixture was stirred at room temperature 15 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 (0.26 g, 26% 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-1a8f3f2deb5e47d6ad77af5351183e75
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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