Hydrochloric Acid → 6-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one

HRID 1847034Notes

Reaction equation

HRID 1847034 reaction equation
C(OC(=O)[NH:7][C@H: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])[N:19](COC)[C:18]=3[CH:27]=2)[CH2:9]1)(C)(C)C.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:7][C@@H: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:27]=2)[C:11](=[O:13])[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86724960{(3S)-1-[4-(methoxymethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-5-oxopyrrolidin-3-yl}carbamic acid tert-butyl ester

Product 1

HCID 867249596-[(4S)-4-Amino-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-oneYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of {(3S)-1-[4-(methoxymethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-5-oxopyrrolidin-3-yl}carbamic acid tert-butyl ester (1.79 g, 4.57 mmol) in tetrahydrofuran (24 ml) was added 6N Hydrochloric acid (11.9 ml) and the mixture was stirred at 80° C. for 1.5 hours. After cooling, the reaction solution was basified by adding a saturated sodium hydrogen carbonate aqueous solution and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, chloroform/methanol) to yield 337 mg (30%) of the title compound in the form of a light yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, chloroform/methanol)

Sources & evidence

ORD record
ord-6398b48f0f7e4aebba9c1f5e32dced0c
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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