Acetic Acid → HCID 66704174, compound

HRID 1661875Notes

Reaction equation

HRID 1661875 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.C(O)(=O)C.C([CH:16]1[C:21](=[O:22])[NH:20][C:18](=[O:19])[C@@:17]1([NH2:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>C(OCC)(=O)C>[CH:7]([NH:28][CH:17]([CH3:18])[CH3:16])([CH3:3])[CH3:6].[CH2:26]([O:25][C:23]([C@@:17]1([N:28]2[CH:3]=[CH:7][CH:6]=[CH:5]2)[CH2:16][C:21](=[O:22])[NH:20][C:18]1=[O:19])=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 66704231HCID 66704231, compound

Product 1

HCID 66704174HCID 66704174, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2,5-Dimethoxytetrahydrofuran (7.4 g) and 2.5% aqueous acetic acid (50 g) were added to ethyl (2R)-2-amino-2-ethoxycarbonylsuccinimide (10 g) and the mixture was stirred at 70° C. for 1.5 hours. The reaction solution was cooled and insoluble materials were dissolved by addition of ethyl acetate (50 ml) and stirring. The mixture was placed for a while and the organic layer was separated from the aqueous layer, washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, diisopropylether (37 g) and ethyl acetate (9.2 g) were added to the residue and diisopropylamine (6.2 g) was added and the mixture was stirred at 0-5° C. of inner temperature. The precipitated crystals were filtered, washed with diisopropylether and dried to give (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt (yield 88%).

Workup

  1. temperatureThe reaction solution was cooled
  2. stirringstirring
  3. customthe organic layer was separated from the aqueous layer
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo, diisopropylether (37 g) and ethyl acetate (9.2 g)
  8. additionwere added to the residue and diisopropylamine (6.2 g)
  9. additionwas added
  10. stirringthe mixture was stirred at 0-5° C. of inner temperature
  11. filtrationThe precipitated crystals were filtered
  12. washwashed with diisopropylether
  13. customdried

Sources & evidence

ORD record
ord-7791410bca1142459fa90a4f8cca7299
Source dataset
uspto-grants-2011_10
Patent number
US08030486B2

Reaction notes

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