Methyl iodide → HCID 90457331, compound

HRID 625868Notes

Reaction equation

HRID 625868 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[H-].[Na+].[CH3:29]COC(C)=O>C1COCC1.O>[CH2:1]([O:8][C:9]([N:11]([CH3:29])[C@H:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 699270851644-83-8

Product 1

HCID 90457331HCID 90457331, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid (1.41 g, 4.18 mmol) and MeI (2.091 mL, 33.4 mmol) in THF (12.66 ml) at 0° C. was slowly added NaH (0.501 g, 12.54 mmol) and the suspension was allowed to stir while warming up to room temperature for 24 hours. The reaction mixture was cooled to 0° C. before 10 mL of EtOAc were added along with 5 mL of water to quench the excess of NaH. The crude product was partitioned between a saturated NaHCO3 aqueous solution and Et2O. The two phases were separated and the organic phase was washed with a saturated NaHCO3 solution and both aqueous extracts were combined. The aqueous solution was brought to pH 3 using a 6N HCl aqueous solution. The aqueous phase was extracted with EtOAc, the organic extracts were combined and dried over anhydrous sodium sulfate. After filtration and concentration, (R)-2-(((benzyloxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid was obtained as a yellow oil, 1.4 g (78%). LCMS showed the m/z of desired product, (M+Na)+ 374.

Workup

  1. customat 0° C.
  2. customto quench the excess of NaH
  3. customThe crude product was partitioned between a saturated NaHCO3 aqueous solution and Et2O
  4. customThe two phases were separated
  5. washthe organic phase was washed with a saturated NaHCO3 solution
  6. extractionThe aqueous phase was extracted with EtOAc
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-715b6c7edd1c45b0b927d520444ac06a
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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