Methyl iodide → HCID 131713506, compound

HRID 638165Notes

Reaction equation

HRID 638165 reaction equation
[CH2:1]([O:3][P:4]([CH2:16][NH:17][C:18]([N:20]1[CH2:34][CH2:33][CH2:32][C@H:21]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:19])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:2].[H-].[Na+].[CH3:37]I>O1CCCC1>[CH3:37][N:17]([CH2:16][P:4]([O:3][CH2:1][CH3:2])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[C:18]([N:20]1[CH2:34][CH2:33][CH2:32][C@H:21]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13603876HCID 13603876, compound

Product 1

HCID 131713506HCID 131713506, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[[[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester (2.43 g., 5 mmole) in dry tetrahydrofuran (15 ml.) is treated with 50% sodium hydride oil dispersion (0.24 g., 5 mmole) and stirred at room temperature for one hour. The mixture is then treated with methyl iodide (0.34 ml., 5.5 mmole) and stirred at room temperature for an additional 3 hours. The mixture is then partitioned between ethyl acetate--5% potassium bisulfate. The organic phase is washed successively with saturated sodium bicarbonate and saturated sodium chloride, dried (Na2SO4) and evaporated. The residue is purified by flash chromatograhy on silica eluting with acetone/dichloromethane (2:3) to give 1-[[methyl[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester.

Workup

  1. stirringstirred at room temperature for an additional 3 hours
  2. customThe mixture is then partitioned between ethyl acetate--5% potassium bisulfate
  3. washThe organic phase is washed successively with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue is purified by flash chromatograhy on silica eluting with acetone/dichloromethane (2:3)

Sources & evidence

ORD record
ord-793224bb6f4b49a794e7918a20de8cea
Source dataset
uspto-grants-1985_12
Patent number
US04560681

Reaction notes

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