Tert-butyl 4-(1-allyloxycarbonylaminocyclopropyl)benzoate → 4-(1-{[(Prop-2-en-1-yloxy)carbonyl]amino}cyclopropyl)benzoic acid

HRID 1921671Notes

Reaction equation

HRID 1921671 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1([C:11]2[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3]>C(#N)C>[CH2:1]([O:4][C:5]([NH:7][C:8]1([C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 59305799Tert-butyl 4-(1-allyloxycarbonylaminocyclopropyl)benzoate

Product 1

HCID 593058104-(1-{[(Prop-2-en-1-yloxy)carbonyl]amino}cyclopropyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.46 g of tert-butyl 4-(1-allyloxycarbonylaminocyclopropyl)benzoate in 10 mL of acetonitrile was combined with 1 g of montmorillonite and refluxed for 3 hours. Then more montmorillonite was added and the mixture was boiled for 4 hours. The suspension was filtered hot, the inorganic material was extracted 3× with hot acetonitrile and filtered off, and the acetonitrile solutions were combined and evaporated down. Residue: 0.8 g of crystals.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe suspension was filtered hot
  3. extractionthe inorganic material was extracted 3× with hot acetonitrile
  4. filtrationfiltered off
  5. customevaporated down

Sources & evidence

ORD record
ord-544d58a635b94750a559f41d56150187
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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