HCID 59075090, compound → HCID 59075102, compound

HRID 2184334Notes

Reaction equation

HRID 2184334 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[CH:18]([OH:32])[C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH:22]=[CH:23][CH:24]=1>CO>[OH:32][CH:18]([C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[CH:22]=[CH:23][CH:24]=1)/[CH:17]=[CH:16]/[C@H:11]1[CH2:12][CH2:13][C:14](=[O:15])[N:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:33])=[O:2]

Participants

3

Reactant 1

HCID 59075090HCID 59075090, compound

Product 1

HCID 59075102HCID 59075102, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution (5 mL) of 7-{(R)-2-[(E)-3-Hydroxy-3-(2′-methyl-biphenyl-3-yl)-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid methyl ester (87 mg) was added an aqueous solution (2.5 mL) of LiOH monohydrate. The reaction mixture was stirred for 6 h and then concentrated to remove the methanol. The aqueous concentrate was diluted with CH2Cl2 and 1N HCl was added, extracted with CH2Cl2 and dried over MgSO4. This mixture was filtered and concentrated to yield 62 mg of 7-{(R)-2-[(E)-3-Hydroxy-3-(2′-methyl-biphenyl-3-yl)-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid as an oil (42) (50).MS:435 [(M+H)+].

Workup

  1. concentrationconcentrated
  2. customto remove the methanol
  3. concentrationThe aqueous concentrate
  4. additionwas diluted with CH2Cl2 and 1N HCl
  5. additionwas added
  6. extractionextracted with CH2Cl2
  7. dry with materialdried over MgSO4
  8. filtrationThis mixture was filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2fb01895f025446585c6a39c65debc9a
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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