Potassium Iodide → HCID 70047673, compound

HRID 280934Notes

Reaction equation

HRID 280934 reaction equation
[C:1]([C@@H:4]([NH:13][C@@H:14]1[C:20](=[O:21])[N:19]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:18]2[CH:30]=[CH:31][CH:32]=[CH:33][C:17]=2[O:16][CH2:15]1)[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([OH:3])=[O:2].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+].[I-].[K+]>CN(C)C=O.O>[CH2:34]([O:2][C:1]([C@@H:4]([NH:13][C@@H:14]1[C:20](=[O:21])[N:19]([CH2:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:18]2[CH:30]=[CH:31][CH:32]=[CH:33][C:17]=2[O:16][CH2:15]1)[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:3])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 54299414HCID 54299414, compound

Product 1

HCID 70047673HCID 70047673, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide is dissolved 0.25 g of tert-butyl 3(S)-[1(S)-carboxy-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate obtained in Example 50, and benzyl bromide (0.14 g), sodium bicarbonate (0.7 g) and potassium iodide (0.05 g) are added to the solution. The reaction solution is stirred at room temperature for 6 hours and diluted with water (100 ml) and extracted with ethyl acetate. The extract is washed successively with 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily product is purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 0.25 g of tert-butyl 3(S)-[1(S)-benzyloxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate as a colorless oil.

Workup

  1. additionare added to the solution
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed successively with 1N hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe oily product is purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-70040de36f9145b79696e950ae7981dc
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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