Ethyl Acetate → HCID 57273049, compound

HRID 1492324Notes

Reaction equation

HRID 1492324 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:31][C@H:30]1[CH2:42][C@H:43]1[CH2:47][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C@H:45]([CH2:55][OH:56])[CH2:44]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(OCC)(=[O:59])C>CN(C)C=O>[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([O:34][Si:35]([C:38]([CH3:39])([CH3:41])[CH3:40])([CH3:37])[CH3:36])[CH2:31][C@H:30]1[CH2:42][C@H:43]1[CH2:47][N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C@H:45]([C:55]([OH:59])=[O:56])[CH2:44]1)=[O:28])([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 57173943HCID 57173943, compound

Product 1

HCID 57273049HCID 57273049, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridinium dichromate was added to a solution of (2R, 4R)-N-tert-butoxycarbonyl-2-[(2S, 4R)-N-tert-butoxycarbonyl-2-(hydroxymethyl)pyrrolidin-4-ylmethyl]-4 -(tert-butyldimethylsiloxy)pyrrolidine (3.00 g, 5.84 mmol, compound of Reference Example 2-6) in N,N-dimethylformamide (30 ml) and stirred at room temperature for 14 hours. Ethyl acetate was added to the reaction solution and washed sequentially with water and a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography (Wakogel™ C-300, 80 ml, n-hexane-ethyl acetate (1:1)) to obtain (2R, 4R)-N-tert-butoxycarbonyl-2-[(2S, 4R)-N-tert-butoxycarbonyl-2-carboxypyrrolidin-4-ylmethyl]-4-(tert-butyldimethylsiloxy)pyrrolidine (1.77 g, yield: 57%).

Workup

  1. washwashed sequentially with water
  2. dry with materiala saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography (Wakogel™ C-300, 80 ml, n-hexane-ethyl acetate (1:1))

Sources & evidence

ORD record
ord-69d3958ce9c8421994726f5f68b0bb40
Source dataset
uspto-grants-1994_12
Patent number
US05373002

Reaction notes

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