Methyl iodide → HCID 59900509, compound

HRID 567851Notes

Reaction equation

HRID 567851 reaction equation
[CH3:1]I.[C:3]([O:7][C:8]([NH:10][CH:11]([C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][CH:32]=1)[CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[C:3]([O:7][C:8]([NH:10][CH:11]([C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][CH:32]=1)[CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:12][O:13][CH3:1])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 59900628HCID 59900628, compound

Product 1

HCID 59900509HCID 59900509, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl iodide (98 ml, 1.57 mmol), benzyl 3-{(1R/S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}phenethylcarbamate (preparation 119) (590 mg, 1.4 mmol), benzyltriethylammonium chloride (325 mg, 1.4 mmol) and NaOH solution (185 ml, 10M, 1.85 mmol) in dichloromethane (10 ml), was stirred at room temperature for 3 days. The reaction mixture was partitioned between dichloromethane and water, the phases separated, and the organic layer dried over MgSO4 and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (0:100 to 50:50) to provide the title compound as a colourless oil, (289 mg, 47%).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. customthe phases separated
  3. dry with materialthe organic layer dried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe residual oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (0:100 to 50:50)

Sources & evidence

ORD record
ord-7e1c259fc8d54aceb6857c540ff74d57
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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