Hydrochloric Acid → (2R)-2-amino-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

HRID 1887742Notes

Reaction equation

HRID 1887742 reaction equation
[CH3:1][CH:2]([CH3:39])[CH2:3][C@@H:4]([NH:31]C(=O)OC(C)(C)C)[C:5](=[O:30])[NH:6][CH:7]1[CH2:16][C:15]2[C:10](=[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[C:8]1=[O:29].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:31][C@H:4]([CH2:3][CH:2]([CH3:39])[CH3:1])[C:5]([NH:6][CH:7]1[CH2:16][C:15]2[C:10](=[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[C:8]1=[O:29])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59620371HCID 59620371, compound

Product 1

HCID 44193593(2R)-2-amino-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl (2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylcarbamate (588 mg) was dissolved in ethanol (2.9 mL), and concentrated hydrochloric acid (1.2 mL) was added thereto. The mixture was heated at 50° C. while being stirred for 30 minutes. The resultant mixture was neutralized with saturated sodium bicarbonate solution under cooling on ice. Subsequently, the mixture was extracted with ethyl acetate, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was washed with saturated sodium chloride solution, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (416 mg) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. extractionSubsequently, the mixture was extracted with ethyl acetate
  3. extractionthe aqueous layer was further extracted with ethyl acetate
  4. washthe combined organic layer was washed with saturated sodium chloride solution
  5. dry with materialby drying over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, whereby the title compound (416 mg)
  7. customwas yielded

Sources & evidence

ORD record
ord-839022d25fda43908cad826a6e0ce15f
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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