Iodoethane → HCID 59999816, compound

HRID 1825327Notes

Reaction equation

HRID 1825327 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:14][CH2:15][C@@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][C:18]([OH:20])=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:29](I)[CH3:30]>O.CO>[CH2:7]([O:14][CH2:15][C@@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17][C:18]([O:20][CH2:29][CH3:30])=[O:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 17999365BOC-D-BETA-HOMOSER(BZL)-OH

Product 1

HCID 59999816HCID 59999816, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of cesium carbonate (3.53 g, 10.9 mmol) in water (22 ml) was added to an ice-cooled solution of (3S)-4-(benzyloxy)-3-[(tert-butoxycarbonyl)amino]butanoic acid (3.36 g, 10.9 mmol) in methanol (70 ml) and water (7 ml), and the reaction stirred for 20 minutes. The mixture was concentrated under reduced pressure and azeotroped with N,N-dimethylformamide and dichloromethane. The residual oil was dissolved in N,N-dimethylformamide (70 ml), ethyl iodide (1.64 g, 10.9 mmol) added, and the reaction stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure, suspended in ethyl acetate (300 ml), washed with water (4×), brine, then dried (MgSO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using hexane:ethyl acetate (85:15) to afford the title compound as a pale yellow oil, 2.86 g; 1H NMR (CDCl3, 400 MHz) δ: 1.26 (t, 3H), 1.45 (s, 9H), 2.65 (d, 2H), 3.58 (m, 2H), 4.17 (m, 3H), 4.55 (s, 2H), 5.20 (bs, 1H), 7.36 (m, 5H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customazeotroped with N,N-dimethylformamide and dichloromethane
  3. dissolutionThe residual oil was dissolved in N,N-dimethylformamide (70 ml)
  4. stirringthe reaction stirred at room temperature for 18 hours
  5. concentrationThe mixture was concentrated under reduced pressure
  6. washwashed with water (4×), brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customThe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7830fe88358b4898a8c9f00edb76c17c
Source dataset
uspto-grants-2006_05
Patent number
US07045653B2

Reaction notes

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