Diethyl Ether → (R)-1-[3-(2-Ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxybenzoyl]pyrrolidine-2-carboxylic acid

HRID 1528160Notes

Reaction equation

HRID 1528160 reaction equation
[CH2:1]([O:3][C:4]1[C:7](=[O:8])[C:6](=[O:9])[C:5]=1[NH:10][C:11]1[C:12]([OH:31])=[C:13]([CH:28]=[CH:29][CH:30]=1)[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[C:21]([O:23]C(C)(C)C)=[O:22])=[O:15])[CH3:2].C(OCC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]1[C:7](=[O:8])[C:6](=[O:9])[C:5]=1[NH:10][C:11]1[C:12]([OH:31])=[C:13]([CH:28]=[CH:29][CH:30]=1)[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@@H:17]1[C:21]([OH:23])=[O:22])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 89534484tert-butyl (R)-1-[3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-benzoyl]pyrrolidine-2-carboxylate

Product 1

HCID 89534485(R)-1-[3-(2-Ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxybenzoyl]pyrrolidine-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.00 g (2.32 mmol) of tert-butyl (R)-1-[3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-benzoyl]pyrrolidine-2-carboxylate were dissolved in 5 ml of trifluoroacetic acid. 25 min later, the reaction medium was concentrated to dryness and was taken up in toluene before being again concentrated. A pink foam was obtained. This foam was taken up with diethyl ether, with stirring, and then filtered. 0.75 g was obtained in the form of a beige solid. Yield=86%.

Workup

  1. concentration25 min later, the reaction medium was concentrated to dryness
  2. concentrationbefore being again concentrated
  3. customA pink foam was obtained
  4. filtrationfiltered
  5. custom0.75 g was obtained in the form of a beige solid

Sources & evidence

ORD record
ord-dd730652fb034539b00bee65bf40a174
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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