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Triethylamine → (S)-tert-butyl 1-((5-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate

HRID 2196512
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HRID 2196512 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[S:15][C:14]([CH2:16][NH2:17])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:18]([F:21])([F:20])[F:19])[CH:7]=1.[NH:22]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:23]([C:25](ON1C(=O)CCC1=O)=[O:26])[CH3:24].C(N(CC)CC)C>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[S:15][C:14]([CH2:16][NH:17][C:25](=[O:26])[C@@H:23]([NH:22][C:35](=[O:36])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH3:24])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:18]([F:20])([F:21])[F:19])[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11011585Boc-Ala-OSuHCID 59843250(5-(5-(Furan-2-yl)-3-(trifluoromethyl)-1h-pyrazol-1-yl)thiophen-2-yl)methanamine

생성물 1

HCID 69095085(S)-tert-butyl 1-((5-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate수율 49.1%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a stirred solution of 23 (crude) (0.588 mmol) in CH2Cl2 (2.9 mL) at 0 degrees were added Boc-Ala-OSu (185 mg, 0.647 mmol) and triethylamine (0.18 mL, 1.3 mmol). The mixture was allowed to reach 21° C. slowly, stirring for 16 h at room temperature. The solvent was then evaporated. The mixture was quenched with a saturated ammonium chloride solution and extracted with ethyl acetate, washed with brine, dried (MgSO4) filtered and concentrated. The residue was purified by silica gel column chromatography with gradient of EtOAc (20-60%) in hexanes to afford 24 (140 mg, 49%) as a white solid. LRMS (ESI): calc. 484.1; found 507.2 (MNa)+.

후처리

  1. customto reach 21° C.
  2. customThe solvent was then evaporated
  3. customThe mixture was quenched with a saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography with gradient of EtOAc (20-60%) in hexanes

출처 및 근거

ORD 기록
ord-d0a0119f2b75459a906fa248a9c0b6a3
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08338437B2

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