Potassium Carbonate → Benzyl L-prolinate

HRID 1789091Notes

Reaction equation

HRID 1789091 reaction equation
C(OC(P(O)(O[C@@H](CCCCNC(OCC1C=CC=CC=1)=O)C([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=O)=O)CC1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCC(C)(C)C([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[NH:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13934665HCID 13934665, compoundHCID 217530474-Chloro-2,2-dimethylbutanoate2×

Product 1

HCID 736155Benzyl L-prolinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[(S)-2-[[[1-(Benzoyloxy)-2-phenylethyl]hydroxyphosphinyl]oxy]-1-oxo-6-[[(phenylmethoxy)carbonyl]amino]hexyl]-L-proline, phenylmethyl ester from Example 5(d) is suspended in dry dimethylformamide and treated with chloromethylpivalate. After several hours, additional chloromethylpivalate and anhydrous potassium carbonate are added and the resulting mixture is stirred overnight. The mixture is then diluted with ethyl acetate and washed successively with water, 5% potassium bisulfate, saturated sodium bicarbonate, and saturated sodium chloride solution, dried (Na2SO4), and evaporated. The residue is purified by flash chromatography (silica gel) to give 1-[(S)-2-[[[(2,2-dimethyl-1-oxopropoxy)methoxy][1-(benzoyloxy)-2-phenylethyl]phosphinyl]oxy]-1-oxo]-6-[[(phenylmethoxy)carbonyl]amino]hexyl]-L-proline, phenylmethyl ester.

Workup

  1. waitAfter several hours
  2. washwashed successively with water, 5% potassium bisulfate, saturated sodium bicarbonate, and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue is purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-af9b398431b84c62bf61834b7fe891d4
Source dataset
uspto-grants-1987_08
Patent number
US04686298

Reaction notes

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