Hydrochloric Acid → HCID 178443480, compound

HRID 355300Notes

Reaction equation

HRID 355300 reaction equation
[Na].Cl.[F:3][C@@H:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[NH:12])=[CH:9][CH:8]=1.C([O:26][C:27](=O)[CH:28]([CH2:34][CH2:35][C@@H:36]([F:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:29](OCC)=[O:30])C.Cl>CO>[OH:26][C:27]1[C:28]([CH2:34][CH2:35][C@@H:36]([F:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[C:29]([OH:30])[N:13]=[C:11]([C:10]2[CH:14]=[CH:15][C:7]([O:6][CH2:5][C@@H:4]([F:3])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:8][CH:9]=2)[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 18666391HCID 18666391, compoundHCID 67576146HCID 67576146, compound

Product 1

HCID 178443480HCID 178443480, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent4×

Procedure

Under nitrogen atmosphere, 2.4 ml of dry methanol was placed in a two-necked round-bottomed flask. To the methanol, 90 mg (3.93 mM) of metal sodium was added and dissolved therein. To the solution, 519 mg (1.57 mM) of (S)-4-(2-fluorodecyloxy)benzamidine hydrochloride was added and stirred for 20 minutes. To the mixture, a solution of 400 mg (1.31 mM) of (S)-2-(3-fluorononyl)malonic diethyl ester in 1 ml of dry methanol was added, followed by stirring for 16 hours at room temperature and distilling-off of methanol under reduced pressure. To the resultant reaction mixture, 4 ml of 6M-HCl was added to precipitate a crystal. The crystal was recovered by filtration and washed with ethanol and Et2O and further dried under reduced pressure. The resultant crystal was recrystallized from DMF to obtain 390 mg (0.77 mM) of 4,6-dihydroxy-5-((3S)-3-fluorononyl)-2-[4-((2S)-2-fluorodecyloxy)phenyl]pyrimidine (Yield: 58.8%).

Workup

  1. dissolutiondissolved
  2. additionwas added
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washwashed with ethanol and Et2O
  6. customfurther dried under reduced pressure
  7. customThe resultant crystal was recrystallized from DMF

Sources & evidence

ORD record
ord-a4730097dc3346f7b44892cb0ef7cb0d
Source dataset
uspto-grants-1998_11
Patent number
US05830386

Reaction notes

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