Acetic Acid → 5-{2-(2-Carboxyethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-(5RS)-5-hydroxypentanoic acid

HRID 55285Notes

Reaction equation

HRID 55285 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=[C:8]([C:27](=[O:34])[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:7]=1)([OH:3])=[O:2].[BH4-].[Na+].C(O)(=O)C.ClCCl>O1CCOCC1.O>[C:1]([CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)=[CH:10][CH:9]=[C:8]([CH:27]([OH:34])[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:7]=1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 199574315-{2-(2-carboxyethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-5-oxopentanoic acid

Product 1

HCID 199574745-{2-(2-Carboxyethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-(5RS)-5-hydroxypentanoic acidYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 20 mg of 5-{2-(2-carboxyethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-5-oxopentanoic acid in 0.9 ml of dioxane and 0.1 ml of water is mixed with 6.5 mg of sodium borohydride and stirred for 2 hours at room temperature. The reaction mixture is mixed with ice water, acidified with glacial acetic acid, shaken out with dichloromethane, the organic phase is dried on sodium sulfate and concentrated by evaporation. The crude product is dissolved in 0.6 ml of methanol, 0.3 ml of 2n sodium hydroxide solution is added, and the mixture is stirred for 48 hours at room temperature. The reaction mixture is concentrated by evaporation, acidified to pH 3 with 2n sulfuric acid, shaken out with ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. 15 mg of the title compound is obtained as colorless oil.

Workup

  1. customthe organic phase is dried on sodium sulfate
  2. concentrationconcentrated by evaporation
  3. dissolutionThe crude product is dissolved in 0.6 ml of methanol
  4. addition0.3 ml of 2n sodium hydroxide solution is added
  5. stirringthe mixture is stirred for 48 hours at room temperature
  6. concentrationThe reaction mixture is concentrated by evaporation
  7. stirringshaken out with ethyl acetate
  8. customthe organic phase is dried on sodium sulfate
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c4fae5214d524b3bbcd8d5287eb16cc5
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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