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 1887767Notes

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

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

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

Sources & evidence

ORD record: ord-5b45015e40dc4b2ca0eb118f99ef59dd
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501772B2

Reaction notes

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