Isopropyl iodide → HCID 60023030, 화합물

HRID 489174노트

반응식

HRID 489174 반응식
[CH2:1]1[CH2:11]CN2C(=NCCC2)C[CH2:2]1.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH:20]([OH:39])/[CH:21]=[CH:22]/[C@H:23]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[N:24]2[CH2:30][C:31]#[C:32][CH2:33][O:34][CH2:35][C:36]([OH:38])=[O:37])[CH:16]=[CH:17][CH:18]=1.IC(C)C>CC(C)=O>[CH:1]([O:37][C:36](=[O:38])[CH2:35][O:34][CH2:33][C:32]#[C:31][CH2:30][N:24]1[C:25](=[O:29])[CH2:26][CH2:27][CH2:28][C@@H:23]1/[CH:22]=[CH:21]/[CH:20]([OH:39])[CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=1)([CH3:11])[CH3:2]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11200577HCID 11200577, 화합물

생성물 1

HCID 60023030HCID 60023030, 화합물수율 60%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

DBU (6.6 μL, 0.044 mmol) was added to a solution of (4-{(R)-2-[(E)4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-6-oxo-piperidin-1-yl)-but-2-ynyloxy)-acetic acid (12 mg, 0.030 mmol) in acetone (0.3 mL). After 5 min, 2-iodopropane (15 μL, 0.15 mmol) was added. After 19 h, the reaction mixture was concentrated in vacuo, 0.5 M aqueous HCl (5 mL) was added and the mixture was extracted with EtOAc (3×5 mL). The combine organic phase was washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL) then dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2 →3% MeOH/CH2Cl2, gradient) afforded 7.9 mg (60%) of the title compound.

후처리

  1. waitAfter 19 h
  2. concentrationthe reaction mixture was concentrated in vacuo, 0.5 M aqueous HCl (5 mL)
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc (3×5 mL)
  5. washThe combine organic phase was washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2 →3% MeOH/CH2Cl2, gradient)

출처 및 근거

ORD 기록
ord-6ee8d4a371e3438c9020c3d3e74bb56d
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977260B2

반응 노트

불러오는 중…