Methyl iodide → HCID 86718363, compound

HRID 1518756Notes

Reaction equation

HRID 1518756 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C@@H:14]([CH:18]([CH2:22][O:23][CH3:24])[CH2:19][O:20][CH3:21])[C:15]([OH:17])=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:25]I.[NH4+].[Cl-]>C1COCC1.CN(C=O)C.C1COCC1>[CH2:3]([O:10][C:11]([N:13]([CH3:25])[C@@H:14]([CH:18]([CH2:22][O:23][CH3:24])[CH2:19][O:20][CH3:21])[C:15]([OH:17])=[O:16])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86718362HCID 86718362, compound

Product 1

HCID 86718363HCID 86718363, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (42 mg, 1.0 mmol, 3.3 equiv) was added in 4 portions to a solution of (S)-2-Benzyloxycarbonylamino-4-methoxy-3-methoxymethyl-butyric acid (100 mg, 0.32 mmol, 1.0 equiv) in dry THF 1 mL at 0° C. After stirring at 0° C. for 10 minutes, it was added a solution of MeI (137 mg, 0.964 mmol, 3.0 equiv) in DMF/THF solution. The mixture was stirred at 0° C. for 1 hour then at room temperature for 16 hours. The reaction mixture was then added to saturated aqueous NH4Cl solution at 0° C. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give product 2.11b (100 mg, 95% yield). The crude material was continued to the next step with no further purification. MS m/z (M+1) 326.3

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hour
  2. waitat room temperature for 16 hours
  3. extractionThe mixture was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b426666da38346288a48e0580274a226
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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