Isopropyl iodide → HCID 60023030、化合物

HRID 489174ノート

反応式

HRID 489174 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 60023030HCID 60023030、化合物収率 60%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6ee8d4a371e3438c9020c3d3e74bb56d
出典データセット
uspto-grants-2005_12
特許番号
US06977260B2

反応ノート

読み込み中…