Pentanoic Acid → HCID 18647421, compound

HRID 345718Notes

Reaction equation

HRID 345718 reaction equation
[OH:1][C@@H:2]([CH3:26])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH3:25])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:9][CH:10]=1.[C:27](O)(=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>ClCCl>[C:27]([O:1][C@@H:2]([CH3:26])[CH2:3][O:4][C:5]1[CH:10]=[N:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH3:25])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:7][CH:6]=1)(=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 7991Pentanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 18647415HCID 18647415, compound

Product 1

HCID 18647421HCID 18647421, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-tetrahydropyranyloxy-1-(p-toluenesulfonyloxy)-propane (192 g, 0.62 mol) prepared in the same manner as in a process described in Example 1 of the specification of Japanese patent application No. Sho 61-133269/1986 in tetrahydrofuran (hereinafter abbreviated to THF) (2,000 ml) was added to a mixture of 60% sodium hydride (31 g, 0.62 mol), 5-hydroxy-2-(4'-propyl-4"-biphenylyl)pyrimidine (150 g, 0.52 mol) and THF (1,200 ml), followed by agitating the resulting mixture at 60° C. for 4 hours, allowing it to cool down to room temperature, adding toluene, washing the resulting organic layer with an alkali and then with water, concentrating it, dissolving the concentrate in ethanol (2,000 ml), adding 6N-hydrochloric acid (40 ml), agitating the mixture at 60° C. for one hour, allowing it to cool down to room temperature, collecting deposited crystals and recrystallizing them from ethyl acetate (1,000 ml) to obtain (S)-5-(2'-hydroxypropyloxy)-2-(4'-propyl-biphenyl-4-yl)-pyrimidine (122 g), which was a liquid crystal and had phase transition points of C-Ch point 161.0° C. and Ch-I point 208.1° C. This (S)-5-(2'-hydroxypropoxy)-2-(4'-propyl-biphenyl-4-yl)pyrimidine (10 g, 0.029 mol), n-pentanoic acid (4.4 g, 0.044 mol), dicyclohexylcarbodiimide (hereinafter abbreviated to DCC) (24 g, 0.12 mol) and dimethylaminopyridine (hereinafter abbreviated to DMAP) (3.9 g) were dissolved in dichloromethane (150 ml), followed by agitating the solution at room temperature for 2 hours, filtering off deposited crystals, washing the filtrate with an alkali and then with water, concentrating it and twice recrystallizing the residue from ethanol (200 ml) to obtain (S)-5-(2'-valeryloxypropoxy)-2-(4'-propyl-biphenyl-4-yl)-pyrimidine (9.8 g).

Workup

  1. customphase transition points of C-Ch point 161.0° C. and Ch-I point 208.1° C
  2. filtrationfiltering off
  3. washwashing the filtrate with an alkali and then with water
  4. concentrationconcentrating it
  5. customtwice recrystallizing the residue from ethanol (200 ml)

Sources & evidence

ORD record
ord-7f6c8df557544c9396fb7878701b8653
Source dataset
uspto-grants-1991_10
Patent number
US05059340

Reaction notes

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