Isopropyl iodide → HCID 131720960, compound

HRID 1455865Notes

Reaction equation

HRID 1455865 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1.I[CH:21]([CH3:23])[CH3:22]>O.CC(O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH2:7][N:8]([CH:21]([CH3:23])[CH3:22])[CH:9]=1

Participants

5

Reactant 2

HCID 6362Isopropyl iodide2×HCID 2734500Boc-3-(3-pyridyl)-D-Ala-OH

Product 1

HCID 131720960HCID 131720960, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Boc-D-Pal (4.0 g, 17.7 mmol) and Ag2O (8.0 g, 34.4 mmol) in 22 ml water was stirred at room temperature for 4 hours. The reaction vessel was cooled to 0° C., and 2-iodopropane (20.4 g, 120 mmol) in 40 ml 2-propanol was added. After addition was complete, the mixture was allowed to warm to room temperature and stirred for 4 days. Additional Ag2O (2 g) and 2-iodopropane (2 g) were added after 24 hours and again after 48 hours. The mixture was filtered, and the precipitate was washed with ethanol (2×15 ml). The filtrate was evaporated to yield 4.3 g of a yellow oil. Crystallization from ethanol/ethyl acetate gave light yellow crystals (3.0 g); Yield: 63%; m.p. 182°-185° C.

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. filtrationThe mixture was filtered
  4. washthe precipitate was washed with ethanol (2×15 ml)
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-fdd83938c574463ba48ac845b07c1c2b
Source dataset
uspto-grants-1998_12
Patent number
US05843901

Reaction notes

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