Triethylamine → HCID 15132640, compound

HRID 467151

Reaction equation

HRID 467151 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])(C)C.[CH2:16](P(C#N)(CC)=O)C.C([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.[CH:31]1C=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:37]([O:40][CH2:41]C)(=[O:39])C>CN(C)C=O>[CH3:16][O:39][CH:37]([O:40][CH3:41])[C@@H:29]1[CH2:30][CH2:28][CH2:27][N:26]1[C:10](=[O:12])[C@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:6]([O:5][CH2:1][C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 13586794DiethylphosphorylcyanideHCID 21583983Benzene ethyl acetate

Product 1

HCID 15132640HCID 15132640, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-prolinal dimethyl acetal hydrochloride obtained in the same manner as in Example 1 is dissolved in dimethylformamide (4 ml) containing tert-butoxycarbonyl-D-proline (790 mg, 3.17 mmol) and diethylphosphoryl cyanide (0.48 ml, 3.16 mmol). To the solution is added dropwise triethylamine (1.15 ml, 8.25 mmol) under cooling and agitation in an ice-methanol bath. The mixture is continued to be stirred for one hour under cooling and then for one hour at room temperature. Benzene-ethyl acetate (2:1, 150 ml) is added to the reaction mixture, and the organic layer is separated, washed successively with a saturated aqueous solution of sodium hydrogen carbonate (15 ml), water (15 ml) and a saturated aqueous solution of edible salt (15 ml), dried over sodium sulfate and filtered. The filtrate is concentrated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel (benzene-ethyl acetate, 1:2→1:1) to give 713 mg (63%) of the title compound as a pale yellow syrup.

Workup

  1. temperatureunder cooling
  2. temperatureunder cooling
  3. waitfor one hour at room temperature
  4. customthe organic layer is separated
  5. washwashed successively with a saturated aqueous solution of sodium hydrogen carbonate (15 ml), water (15 ml)
  6. dry with materiala saturated aqueous solution of edible salt (15 ml), dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated to dryness under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel (benzene-ethyl acetate, 1:2→1:1)

Sources & evidence

ORD record
ord-fa19b9577d11491c9393047d151120d8
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Linked notes

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