Trifluoroacetic acid → 6-(4-Amino-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1846994Notes

Reaction equation

HRID 1846994 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=3[CH:24]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH:8]1[CH2:9][N:10]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][C:20](=[O:23])[NH:19][C:18]=3[CH:24]=2)[C:11](=[O:13])[CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724925[5-Oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

Product 1

HCID 824984066-(4-Amino-2-oxopyrrolidin-1-yl)-2H-1,4-benzoxazin-3(4H)-oneYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[5-Oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (1.02 g, 2.94 mmol) was added to a solution mixture of trifluoroacetic acid (10 ml) and dichloromethane (10 ml), and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, the obtained residue was dissolved in water and neutralized by adding a saturated sodium hydrogen carbonate aqueous solution. The solvent of the mixture was removed under reduced pressure and the obtained residue was purified by NH-silica gel column chromatography (chloroform/methanol) to yield 642 mg (88%) of the title compound in the form of a light brown solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in water
  3. additionby adding a saturated sodium hydrogen carbonate aqueous solution
  4. customThe solvent of the mixture was removed under reduced pressure
  5. customthe obtained residue was purified by NH-silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-2f2c14b9381043fe872d9fca7fa3e454
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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