Iodoethane → HCID 67774565, compound

HRID 1808845Notes

Reaction equation

HRID 1808845 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]([C@@H:10]([CH2:17][CH2:18][CH3:19])[CH2:11][N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)[CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:25][CH3:26].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([C@@H:10]([CH2:17][CH2:18][CH3:19])[CH2:11][N:12]2[CH2:15][CH:14]([O:16][CH2:25][CH3:26])[CH2:13]2)[CH3:9])=[O:7])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57345459HCID 57345459, compound

Product 1

HCID 67774565HCID 67774565, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (S)-4-chloro-N-(1-(3-hydroxyazetidin-1-yl)pentan-2-yl)-N-methylbenzamide (Example 8.2 A) (85 mg, 0.27 mmol) in dry THF (3 mL) was NaH (60% in mineral oil) (16.41 mg, 0.41 mmol) added carefully. The mixture was stirred at rt for 30 minutes then iodoethane (0.023 mL, 0.29 mmol) was added in one portion. The mixture was left standing at rt on. NaHCO3 and DCM were added and the two layers were separated using a phase separator. The organic phase was concentrated and the residue was purified by preparative HPLC to give the title compound (36 mg, 39%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.71, 0.86, 0.93-1.08, 1.08-1.32, 1.33-1.49, 2.36, 2.49-2.53, 2.54-2.61, 2.66, 2.70, 2.72-2.80, 3.19-3.32, 3.48, 3.96, 7.32, 7.38, 7.47. HRMS (M+H)+: calculated 339.1839. found 339.1840.

Workup

  1. additionadded carefully
  2. waitThe mixture was left
  3. customstanding at rt
  4. customthe two layers were separated
  5. concentrationThe organic phase was concentrated
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-56f1e70df94e4b37a0b008f76897306e
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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