Methyl iodide → HCID 57089148, compound

HRID 379013Notes

Reaction equation

HRID 379013 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:25])[NH:9][C@@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:11]([C:13](=[O:17])[N:14]([CH3:16])[CH3:15])[OH:12])([CH3:6])([CH3:5])[CH3:4].[CH3:26]I.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:3]([O:7][C:8](=[O:25])[NH:9][C@@H:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:11]([C:13](=[O:17])[N:14]([CH3:15])[CH3:16])[O:12][CH3:26])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 57322262HCID 57322262, compound

Product 1

HCID 57089148HCID 57089148, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride-oil dispersion (53 mg of 50%) was added to a solution of (1S,2R)-(1-benzyl-2-dimethylcarbamoyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester (322 mg, 1.0 mmol) in tetrahydrofuran (4 mL) at 0° C. After effervescence ceased (several minutes), methyl iodide (155 mg) was added, and after 15 minutes another 11 mg NaH dispersion and 23 mg methyl iodide were added. After 15 more minutes aqueous ammonium chloride solution and ethyl acetate were added, and the organic layer was separated, washed with water, 2N NaOH, dried and concentrated giving a viscous oil which was used without further purification: Yield 283 mg, 84%.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water, 2N NaOH
  4. customdried
  5. concentrationconcentrated
  6. customgiving a viscous oil which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-4e56b40b826444909f2ca9630e406224
Source dataset
uspto-grants-2001_10
Patent number
US06297269B1

Reaction notes

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