Water → 7-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-(methacryloyloxy)-acetate

HRID 558051Notes

Reaction equation

HRID 558051 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]1[CH:10]2[O:11][C:12](=[O:22])[CH:13]3[CH:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]1[CH2:8][CH:9]23)=[O:4].[C:23]([OH:28])(=[O:27])[C:24]([CH3:26])=[CH2:25].C(N(CC)CC)C.O>CN(C)C=O.[I-].[Na+]>[C:23]([O:28][CH2:2][C:3]([O:5][CH:6]1[CH:10]2[O:11][C:12](=[O:22])[CH:13]3[CH:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]1[CH2:8][CH:9]23)=[O:4])(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

7

Reactant 4

HCID 962WaterHCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 579457837-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-chloroacetate

Product 1

HCID 250640817-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-(methacryloyloxy)-acetateYield 91.3%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

In 800 ml of dimethylformamide were dissolved 199 g of the 2-chloroacetate obtained in Example 1-6-1, 64.8 g of methacrylic acid, and 4.50 g of sodium iodide. To the solution below 30° C., 73.1 g of triethylamine was added dropwise. The reaction solution was stirred at the temperature overnight, whereupon 500 ml of deionized water below 30° C. was added, followed by ordinary workup. Recrystallization from hexane yielded 209 g of the title compound. Yield 91%.

Workup

  1. additionwas added
  2. customRecrystallization from hexane

Sources & evidence

ORD record
ord-6f967edc91f449159ffd293f1f51a006
Source dataset
uspto-grants-2011_11
Patent number
US08062831B2

Reaction notes

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