Methyl iodide → HCID 59134383, compound

HRID 2425358Notes

Reaction equation

HRID 2425358 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([C@H:17]2[C:30]3[CH:29]=[C:28]4[C:23]([NH:24][C:25](=[O:31])[CH2:26][O:27]4)=[CH:22][C:21]=3[O:20][C:19]([CH3:33])([CH3:32])[C@@H:18]2[OH:34])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:35](=O)([O-])[O-].[K+].[K+].CI.[Cl-].[NH4+]>CN(C)C=O>[C:1]1([CH2:7][CH2:8][N:9]([C@H:17]2[C:30]3[CH:29]=[C:28]4[C:23]([N:24]([CH3:35])[C:25](=[O:31])[CH2:26][O:27]4)=[CH:22][C:21]=3[O:20][C:19]([CH3:33])([CH3:32])[C@@H:18]2[OH:34])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 59240713HCID 59240713, compound

Product 1

HCID 59134383HCID 59134383, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of t-butyl (2-phenylethyl)(7R*,8S*)-[7-hydroxy-6,6-dimethyl-3-oxo-2,3,4,6,7,8-hexahydro-1,5-dioxa-4-aza-anthracene-8-yl]carbamate (106 mg, 0.23 mmol) in dimethylformamide (2 mL), potassium carbonate (79 mg, 0.57 mmol) and methyl iodide (28 δL, 0.46 mmol) were added at room temperature, and the resulting mixture was stirred at room temperature for 4 hours. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=2/1) and the aimed product was obtained (yield: 100%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-21863783b43d4e8d82fbfda832071c75
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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