Miridesap → HCID 69463158, compound

HRID 1070899Notes

Reaction equation

HRID 1070899 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)C=C>[CH2:8]([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][CH2:11][CH:10]=[CH2:9])=[O:2])=[O:24])=[O:23])[CH:4]=[CH2:1]

Participants

3

Reactant 1

HCID 125516Miridesap

Product 1

HCID 69463158HCID 69463158, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

A mixture of 1.02 g (3 mmol) (R)-1-[6-[(R)-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid and 3 g Amberlite® IR120 in 30 ml allylalcohol were stirred at room temperature for 90 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 620 mg (49%) (R)-1-{6-[(R)-2-alloxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid allyl ester as alight yellow oil, MS m/e (%): 421 (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-cec944578c6c4135b3692db41ccaedec
Source dataset
uspto-grants-2005_06
Patent number
US06903129B2

Reaction notes

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