Methyl iodide → HCID 86670474, compound

HRID 1911858Notes

Reaction equation

HRID 1911858 reaction equation
[Si:1]([O:8][C@H:9]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:32])[NH:23][CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH3:25])=[CH:18][CH:17]=2)[N:11]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH3:48]I>O1CCCC1>[Si:1]([O:8][C@H:9]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:32])[N:23]([CH3:48])[CH:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH3:25])=[CH:18][CH:17]=2)[N:11]1[C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86670473HCID 86670473, compound

Product 1

HCID 86670474HCID 86670474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-(4-{[1-(pyridine-2-yl)ethyl]carbamoyl}benzyl)pyrrolidine-1-carboxylate (350 mg, 0.556 mmol) in tetrahydrofuran (1.1 mL), was added sodium hydride (26.7 mg of a 60 wt % dispersion, 0.667 mmol) at 0° C. The reaction was stirred for 30 minutes before methyl iodide (38.2 μl, 0.611 mmol) was added. The resulting red colored reaction was stirred for 3 hours before being quenched by pouring into a separatory funnel containing water and was extracted with ethyl acetate (3×50 mL). The organic extracts were combined and dried with Na2SO4, filtered, and evapourated in vacuo and taken directly to the next step. LC-MS=644.3 (M+1)+.

Workup

  1. additionwas added
  2. customThe resulting red colored reaction
  3. custombefore being quenched
  4. additionby pouring into a separatory funnel
  5. additioncontaining water
  6. extractionwas extracted with ethyl acetate (3×50 mL)
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-2892990d9c1f4cab908b67d2a68e1760
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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