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 2070169Notes

Reaction equation

HRID 2070169 reaction equation
Cl.[CH3:2][CH:3]([CH3:40])[CH2:4][C@@H:5]([NH:32]C(=O)OC(C)(C)C)[C:6](=[O:31])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[C:12]([N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[C:9]1=[O:30].[OH-].[Na+]>O1CCCC1>[NH2:32][C@H:5]([CH2:4][CH:3]([CH3:40])[CH3:2])[C:6]([NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[C:12]([N:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[C:9]1=[O:30])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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 8028TetrahydrofuranSolvent

Conditions

Temperature
48 °C

Procedure

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

Workup

  1. temperatureunder cooling on an ice bath
  2. customthe organic layer was separated

Sources & evidence

ORD record
ord-2f5c3e5298df4f049a339c67ebf80b81
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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