HCID 23204297, compound → HCID 22010361, compound

HRID 322881Notes

Reaction equation

HRID 322881 reaction equation
[C:1]([C:4]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[N:32][CH:33]=2)=[CH:22][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])(=[O:3])[CH3:2]>O1CCOCC1.[OH-].[Na+]>[C:1]([C:4]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[N:32][CH:33]=2)=[CH:22][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 23204297HCID 23204297, compound

Product 1

HCID 22010361HCID 22010361, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl (RS)-4-[2-acetyl-5-(5-pyrimidinylmethoxy)phenoxy]-4-(2-methylphenyl)-butanoate (1.1 g) in dioxan (10 mL) and sodium hydroxide (5.3 mL; 1 M) is stirred at 25° C. for 45 minutes. The solution is evaporated, the residue is diluted with water, and brought to pH 6 by treatment with hydrochloric acid (2 M). The precipitate is extracted with ethyl acetate, washed with water, dried and evaporated. The residual oil is subjected to flash chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5 v/v), followed by trituration with diethyl ether to give (RS)-4-(2-acetyl-5-(5-pyrimidinylmethoxy)-phenoxy]-4-(2-methylphenyl)butanoic acid (0.44 g) in the form of a colourless solid, m.p.142-144° C. [NMR(CDCl3):- 2.2-2.7(4H,m),2.45(3H,s), 2.7 (3H,s),4.9(2H,q),5.5(1H,q),6.2-7.8(7H),8.7(2H,s), 9.2(1H,s)].

Workup

  1. customThe solution is evaporated
  2. additionthe residue is diluted with water
  3. extractionThe precipitate is extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. washeluting with a mixture of dichloromethane and methanol (95:5 v/v)

Sources & evidence

ORD record
ord-a242d186c8c04a4d8c6c4c802575080b
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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