Triethylamine → HCID 22856154, compound

HRID 2399962Notes

Reaction equation

HRID 2399962 reaction equation
[OH:1][C@H:2]([CH2:7][C@H:8](O)[CH2:9][CH2:10][C@@H:11]1[C@@H:20]2[C:15](=[CH:16][C@@H:17]([OH:22])[CH2:18][C@@H:19]2[OH:21])[CH:14]=[CH:13][C@@H:12]1[CH3:23])[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>O1CCCC1>[OH:22][C@H:17]1[CH2:18][C@H:19]([OH:21])[C@H:20]2[C:15]([CH:14]=[CH:13][C@H:12]([CH3:23])[C@@H:11]2[CH2:10][CH2:9][C@H:8]2[O:5][C:4](=[O:6])[CH2:3][C@H:2]([OH:1])[CH2:7]2)=[CH:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 22856170DES(2-methylbutanoyl)pravastatin

Product 1

HCID 22856154HCID 22856154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The whole of the crude (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoic acid, prepared as described in Step 2, above, was mixed with 1000 ml of tetrahydrofuran. 38 ml (0.27 mol) of triethylamine were then added to the mixture, followed by 38 ml (0.25 mol) of diethyl cyanophosphonate, whilst ice-cooling and stirring. The resulting mixture was then stirred at room temperature for 1.5 hours. At the end of this time, the tetrahydrofuran was removed from the reaction mixture by distillation under reduced pressure and the residue was triturated with a mixture of diethyl ether and ethanol to stimulate crystallization. The resulting crystals were collected by filtration to provide 47.7 g of the title compound. This was then recrystallized from a mixture of ethyl acetate and ethanol to produce colorless plates melting at between 161° and 163° C.

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was then stirred at room temperature for 1.5 hours
  3. customAt the end of this time, the tetrahydrofuran was removed from the reaction mixture by distillation under reduced pressure
  4. customthe residue was triturated with a mixture of diethyl ether and ethanol
  5. customcrystallization
  6. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-2403521058f0472b9bb6f69a525e63ef
Source dataset
uspto-grants-1995_09
Patent number
US05451688

Reaction notes

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