Water → HCID 67181701, 화합물

HRID 1801467

반응식

HRID 1801467 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:11]([O:13][C:14](=[O:25])[CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH3:12].Br[CH2:27][C:28]1[C:29]([F:40])=[CH:30][CH:31]=[C:32]2[C:37]=1[N:36]=[C:35]([O:38][CH3:39])[CH:34]=[CH:33]2.O>C1COCC1.CC(=O)OCC>[CH2:11]([O:13][C:14](=[O:25])[CH:15]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:27][C:28]1[C:29]([F:40])=[CH:30][CH:31]=[C:32]2[C:37]=1[N:36]=[C:35]([O:38][CH3:39])[CH:34]=[CH:33]2)[CH3:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 15933116Ethyl 3-{[(tert-butoxy)carbonyl]amino}propanoateHCID 66737650HCID 66737650, 화합물

생성물 1

HCID 67181701HCID 67181701, 화합물수율 75%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of LiHMDS (1M, 20 mL), cooled to −78° C., was added dropwise a solution of 3-tert-butoxycarbonylamino-propionic acid ethyl ester (2.01 g, 9.26 mmol; prepared as in Tetrahedron Lett. (2003), 44(14), 2807) in THF (20 mL). The solution was stirred at the same temperature for 90 min. A solution of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (2.5 g; prepared as in WO 2007/081597) in THF (10 mL) was quickly added and the reaction proceeded for 2 h, keeping the internal temperature below −50° C. Water (100 mL) and EA (200 mL) were added. The two layers were separated and the aq. layer was extracted with EA. The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 2:1) to afford the title intermediate as a pale yellow oil, which solidified (2.83 g, 75% yield) after standing at rt for one day.

후처리

  1. waitthe reaction proceeded for 2 h
  2. customthe internal temperature below −50° C
  3. customThe two layers were separated
  4. extractionthe aq. layer was extracted with EA
  5. washlayers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by CC (Hept-EA 2:1)

출처 및 근거

ORD 기록
ord-c276b53a2bc54b6d8a5902f66bd2b4aa
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349828B2

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