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 2070171Notes

Reaction equation

HRID 2070171 reaction equation
Cl.[CH3:2][C:3]([NH:39]C(=O)OC(C)(C)C)([CH3:38])[C:4]([NH:6][C@H:7]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:8](=[O:33])[NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:5].[OH-].[Na+]>O1CCCC1>[NH2:39][C:3]([CH3:2])([CH3:38])[C:4]([NH:6][C@H:7]([CH2:34][CH:35]([CH3:36])[CH3:37])[C:8]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:33])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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 8028TetrahydrofuranSolvent

Conditions

Temperature
48 °C

Procedure

Concentrated hydrochloric acid (89.6 mL) was added to the tetrahydrofuran solution of 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, and the mixture was stirred at an internal temperature of 48±2° C. for 30 minutes. The mixture was neutralized with 25% aqueous sodium hydroxide solution (172 g) under cooling on an ice bath. The organic layer was separated, and then concentrated under reduced pressure, whereby the title compound (49.36 g) was yielded.

Workup

  1. temperatureunder cooling on an ice bath
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure, whereby the title compound (49.36 g)
  4. customwas yielded

Sources & evidence

ORD record
ord-a4bc1a72ccee4f6086f6a142975b1444
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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