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

HRID 1952581노트

반응식

HRID 1952581 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14]([OH:16])=O)=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[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:58]([Si:62]([CH3:73])([CH3:72])[O:63][C:64]1[CH:65]=[C:66]([CH:69]=[CH:70][CH:71]=1)[CH2:67][NH2:68])([CH3:61])([CH3:60])[CH3:59]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:14](=[O:16])[NH:68][CH2:67][C:66]2[CH:69]=[CH:70][CH:71]=[C:64]([O:63][Si:62]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:72])[CH3:73])[CH:65]=2)=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])=[O:4]

참가 물질

7

반응물 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 682266025-(Methoxycarbonyl)-4-(trifluoromethyl)thiophene-2-carboxylic acid

생성물 1

HCID 682271015-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester수율 20.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-Trifluoromethyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (560 mg, 2.20 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.92 mL, 6.6 mmol), HBTU (1.0 g, 2.64 mmol), HOBT (360 mg, 2.64 mmol), and 3-(tert-Butyl-dimethyl-silanyloxy)-benzylamine (630 mg, 2.64 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 0-40% EtOAc in hexane to afford the desired product (0.21 g, 20% yield).

후처리

  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 0-40% EtOAc in hexane

출처 및 근거

ORD 기록
ord-ac7fc72a3f7e4ac39497d871d3d6c0b4
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404859B2

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