Isopropyl iodide → HCID 59280238, compound

HRID 505488Notes

Reaction equation

HRID 505488 reaction equation
N12CCCN=C1CC[CH2:4][CH2:3][CH2:2]2.IC(C)C.[OH:16][C@H:17]([C:23]1[CH:28]=[CH:27][C:26]([N:29]2[C:33](=[O:34])[CH2:32][O:31][C@@H:30]2[CH2:35][CH2:36][CH2:37][C:38]2[S:42][C:41]([C:43]([OH:45])=[O:44])=[CH:40][CH:39]=2)=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CC(C)=O>[OH:16][C@H:17]([C:23]1[CH:24]=[CH:25][C:26]([N:29]2[C:33](=[O:34])[CH2:32][O:31][C@@H:30]2[CH2:35][CH2:36][CH2:37][C:38]2[S:42][C:41]([C:43]([O:45][CH:3]([CH3:4])[CH3:2])=[O:44])=[CH:40][CH:39]=2)=[CH:27][CH:28]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 25205537HCID 25205537, compound

Product 1

HCID 59280238HCID 59280238, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU, 5.5 μL, 0.037 mmol) and 2-iodopropane (65 μL, 0.65 mmol) were added to a solution of acid 12i (8 mg, 0.019 mmol) in acetone (0.19 mL) at rt under nitrogen. After 3 d at room temperature, the volatiles were evaporated under a stream of nitrogen. The residue was diluted with water (1 mL), acidified with 1.0 N HCl (1 mL) and extracted with EtOAc (3×10 mL). The combined extracts were washed with brine (5 mL), then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on 4 g silica (hexanes→EtOAc, gradient) afforded 6.5 mg (74%) of 12j.

Workup

  1. customthe volatiles were evaporated under a stream of nitrogen
  2. additionThe residue was diluted with water (1 mL)
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined extracts were washed with brine (5 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography on 4 g silica (hexanes→EtOAc, gradient)

Sources & evidence

ORD record
ord-fb4fafc2220e4fb388e3caceaf506043
Source dataset
uspto-grants-2010_08
Patent number
US07781465B2

Reaction notes

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