2-Methyl-2-butene → HCID 67490923, compound

HRID 1917389Notes

Reaction equation

HRID 1917389 reaction equation
CC(=CC)C.[C:6]([O:10][C:11]([C@@:13]1([CH2:36][CH:37]=[O:38])[C@@H:17]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:27])[N:15]([C@@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:29])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].Cl([O-])=[O:40].[Na+].O.O.P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[C:6]([O:10][C:11]([C@@:13]1([CH2:36][C:37]([OH:40])=[O:38])[C@@H:17]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:27])[N:15]([C@@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:29])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86664652HCID 86664652, compound

Product 1

HCID 67490923HCID 67490923, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2-Methyl-2-butene was added to a solution of (3S,4S)-4-benzyloxymethyl-5-oxo-3-(2-oxoethyl)-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (4.58 g, 10.1 mmol) in tert-butyl alcohol (25.2 mL) under ice-cooling, and the mixture was stirred. Sodium chlorite (2.29 g, 25.3 mmol) was added to a solution of sodium dihydrogenphosphate dihydrate (4.10 g, 26.3 mmol) in water (20.2 mL) to separately prepare a solution. This solution was added to the above solution under ice-cooling, and the mixture was stirred at room temperature for one hour. The precipitated solid was collected by filtration, washed with water and hexane, and then dried under reduced pressure at 40° C. to give 3.93 g of the title compound as white powder crystals.

Workup

  1. temperaturecooling
  2. customto separately prepare a solution
  3. additionThis solution was added to the above solution under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for one hour
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water and hexane
  8. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-a37e0dc416ca4cee9b31e76ef3739920
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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