Methyl iodide → HCID 21940430, compound

HRID 1243137Notes

Reaction equation

HRID 1243137 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:19]([OH:21])=[O:20])[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[H-].[Na+].[C:26](OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH3:26])[C:9]1([C:19]([OH:21])=[O:20])[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27331772-[(tert-Butoxycarbonyl)amino]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 21940430HCID 21940430, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-tert-butoxycarbonylamino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (291 mg, 1.0 mmol) in DMF (2.0 mL) was added MeI (710 mg, 5.0 mmol) and NaH (50%, 250 mg, 5.0 mmol) at 0° C. Ethyl acetate (50 mL) was added after 3 days and the mixture was washed with water (3×15 mL). The material (380 mg) was taken up in methanol (5.0 mL) and water (3.0 mL) and NaOH (10 M, 3.0 mL) was added. After 2 days, 10% HCl was added to adjust the pH˜2 and the mixture was extracted with ethyl acetate (3×20 mL). The organic layers were concentrated in vacuo to provide the titled acid.

Workup

  1. washthe mixture was washed with water (3×15 mL)
  2. additionwater (3.0 mL) and NaOH (10 M, 3.0 mL) was added
  3. addition10% HCl was added
  4. extractionthe mixture was extracted with ethyl acetate (3×20 mL)
  5. concentrationThe organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-1c95195afe6a497db876ec98accdeaf4
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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