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

HRID 2070155Notes

Reaction equation

HRID 2070155 reaction equation
[CH3:1][C:2]([NH:38]C(=O)OC(C)(C)C)([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7](=[O:32])[NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[C:10]1=[O:31])=[O:4].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:38][C:2]([CH3:1])([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[C:10]1=[O:31])=[O:32])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 44193590tert-butyl 2-methyl-1-[(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-ylamino]-1-oxopropan-2-ylcarbamate

Product 1

HCID 59620332(2R)-2-(2-amino-2-methylpropanamido)-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
70 °C

Procedure

tert-Butyl 2-methyl-1-[(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-ylamino]-1-oxopropan-2-ylcarbamate (2.8 g) was dissolved in ethanol (28 mL), and concentrated hydrochloric acid (7.5 mL) was added thereto. The mixture was heated at 70° C. while being stirred for 30 minutes, and then neutralized with saturated aqueous sodium bicarbonate solution under cooling on ice. Subsequently, the resultant mixture was extracted with chloroform and water, and the aqueous layer was further extracted with chloroform. The organic layers were combined. The combined organic layer was washed with saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (2.30 g) was yielded.

Workup

  1. temperatureunder cooling on ice
  2. extractionSubsequently, the resultant mixture was extracted with chloroform and water
  3. extractionthe aqueous layer was further extracted with chloroform
  4. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, whereby the title compound (2.30 g)
  7. customwas yielded

Sources & evidence

ORD record
ord-f056f480449e442587217f5fe062fefb
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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