Benzyl L-prolinate → HCID 13118410, compound

HRID 1649346Notes

Reaction equation

HRID 1649346 reaction equation
[CH2:1]([O:3][P:4]([CH2:24][C:25](O)=[O:26])([CH:6]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[NH:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C(#N)C>[CH2:1]([O:3][P:4]([CH2:24][C:25]([N:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])=[O:26])([CH:6]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 736155Benzyl L-prolinateHCID 13118408HCID 13118408, compound

Product 1

HCID 13118410HCID 13118410, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of the product from part (d) (834 mg., 2.15 mmole) in dry acetonitrile (8 ml.) is treated with N,N'-carbonyldiimidazole (375 mg., 2.31 mmole) and stirred at 0° (ice bath) under argon for 1.5 hours. The resulting solution is then treated with L-proline, benzyl ester (455 mg., 2.22 mmole) in acetonitrile and stirred at room temperature for 4 hours. The mixture is evaporated to dryness and the residue is taken up in ethyl acetate. The ethyl acetate solution is washed successively with 5% potassium bisulfate, saturated sodium bicarbonate and saturated sodium chloride, dried over Na2SO4 and evaporated. The residue (1.325 g.) is purified by flash chromatography on silica gel (75 g.) eluting with 1% methanol/dichloromethane to give (±)-1-[[ethoxy[3-oxo-3-phenyl-1-(2-phenylethyl)propyl]phosphinyl]acetyl]-L-proline, phenylmethyl ester (74%) as a colorless glass, Rf (methanol/dichloromethane; 5:95) 0.29.

Workup

  1. stirringstirred at room temperature for 4 hours
  2. customThe mixture is evaporated to dryness
  3. washThe ethyl acetate solution is washed successively with 5% potassium bisulfate, saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue (1.325 g.) is purified by flash chromatography on silica gel (75 g.)
  7. washeluting with 1% methanol/dichloromethane

Sources & evidence

ORD record
ord-8a41ac239a1d4ad5a5cfdde0fb6267d3
Source dataset
uspto-grants-1983_11
Patent number
US04416833

Reaction notes

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