Miridesap → HCID 69463152, compound

HRID 1070901Notes

Reaction equation

HRID 1070901 reaction equation
[C:1]([C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[C:21]([OH:23])=[O:22])=[O:15])([OH:3])=[O:2]>C(O)CCC=C>[CH2:1]([O:22][C:21]([C@H:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@@H:4]1[C:1]([O:3][CH2:13][CH2:12][CH2:11][CH:10]=[CH2:9])=[O:2])=[O:24])=[O:23])[CH2:4][CH2:8][CH:7]=[CH2:6]

Participants

3

Reactant 1

HCID 125516Miridesap

Product 1

HCID 69463152HCID 69463152, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 131814-Penten-1-OLSolvent

Procedure

A mixture of 2.04 g (6 mmol) (R)-1-[6-[(R)-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid and 5 g Amberlite® IR120 in 25 ml 4-penten-1-ol were stirred at room temperature for 48 hours. After filtration the solvent was distilled off, the residue was taken up in dichloromethane and extracted with 2% aqueous sodium bicarbonate. The organic extract was dried with sodium sulfate and the solvent was distilled off to yield 1.6 g (58%) (R)-1-[6-[(R)-2-pent-4-enyloxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid pent-4-enyl ester as a light yellow oil, MS m/e (%): 477 (M+H+, 100).

Workup

  1. filtrationAfter filtration the solvent
  2. distillationwas distilled off
  3. extractionextracted with 2% aqueous sodium bicarbonate
  4. extractionThe organic extract
  5. dry with materialwas dried with sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6e843262117a4f3390daedfcb7b98a69
Source dataset
uspto-grants-2005_06
Patent number
US06903129B2

Reaction notes

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