Hydrochloric Acid → HCID 178442766, compound

HRID 355298Notes

Reaction equation

HRID 355298 reaction equation
[Na].Cl.[CH2:3]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[NH:18])=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([O:24][C:25](=O)[CH:26]([CH2:32][CH2:33][C@@H:34]([F:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:27](OCC)=[O:28])C.Cl>CO>[OH:24][C:25]1[C:26]([CH2:32][CH2:33][C@@H:34]([F:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:27]([OH:28])[N:19]=[C:17]([C:16]2[CH:15]=[CH:14][C:13]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:21][CH:20]=2)[N:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 18666391HCID 18666391, compoundHCID 18941670HCID 18941670, compound

Product 1

HCID 178442766HCID 178442766, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent4×

Procedure

Under nitrogen atmosphere, 3 ml of dry methanol was placed in a two-necked round-bottomed flask. To the methanol, 113 mg (4.92 mM) of metal sodium was added and dissolved therein. To the solution, 584 mg (1.97 mM) of 4-decylbenzamidine hydrochloride was added and stirred for 20 minutes. To the mixture, a solution of 500 mg (1.64 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. The resultant crystal was recrystallized from 2.5 ml of N,N-dimethylformamide (DMF) to obtain 428 mg (0.91 mM) of (S)-4,6-dihydroxy-5-(3-fluorononyl)-2-(4-decylphenyl)pyrimidine (Yield: 55.3%).

Workup

  1. dissolutiondissolved
  2. additionwas added
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. washwashed with ethanol and Et2O and further dried
  6. customThe resultant crystal was recrystallized from 2.5 ml of N,N-dimethylformamide (DMF)

Sources & evidence

ORD record
ord-5fcb9215887c486799f8415f55971d20
Source dataset
uspto-grants-1998_11
Patent number
US05830386

Reaction notes

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