Isopropyl iodide → HCID 69020306, compound

HRID 349364Notes

Reaction equation

HRID 349364 reaction equation
[CH2:1]1[CH2:11]CN2C(=NCCC2)C[CH2:2]1.[OH:12][CH:13]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)/[CH:14]=[CH:15]/[C@H:16]1[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[N:17]1[CH2:23][C:24]#[C:25][CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30].IC(C)C>CC(C)=O.CCOC(C)=O>[CH:1]([O:30][C:29](=[O:31])[CH2:28][O:27][CH2:26][C:25]#[C:24][CH2:23][N:17]1[C:18](=[O:22])[CH2:19][CH2:20][CH2:21][C@@H:16]1/[CH:15]=[CH:14]/[CH:13]([OH:12])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([CH3:11])[CH3:2]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69022915HCID 69022915, compound

Product 1

HCID 69020306HCID 69020306, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

DBU (10 μL, 0.067 mmol) was added to a solution of {4-[(R)-2-((E)-3-hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-but-2-ynyloxy}-acetic acid (16.6 mg, 0.045 mmol) in acetone (0.5 mL). After 5 min, 2-iodopropane (22.5 μL, 0.225 mmol) was added. After 18 h, the reaction mixture was diluted with EtOAc (25 mL) and washed sequentially with aqueous HCl (0.1 M, 10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford 10.6 mg (57%) of the title compound.

Workup

  1. waitAfter 18 h
  2. washwashed sequentially with aqueous HCl (0.1 M, 10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea8679b5bede4c96bac904c1439572a4
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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