Hydrochloric Acid → HCID 59620347, compound

HRID 1887776Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]([CH2:18][C:19]1[CH:23]=[CH:22][S:21][CH:20]=1)[C:15](=[O:24])[CH:14]([NH:25][C:26](=[O:46])[C@H:27]([NH:32][C:33](=[O:45])[C:34]([NH:37]C(=O)OC(C)(C)C)([CH3:36])[CH3:35])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:13]2.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:37][C:34]([CH3:35])([CH3:36])[C:33]([NH:32][C@H:27]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:26]([NH:25][CH:14]1[CH2:13][C:12]2[C:17](=[C:8]([N:3]3[C:2](=[O:1])[CH2:6][CH2:5][C:4]3=[O:7])[CH:9]=[CH:10][CH:11]=2)[N:16]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:15]1=[O:24])=[O:46])=[O:45]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 1-((2R)-1-(8-(2,5-dioxopyrrolidin-1-yl)-2-oxo-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (30 mg) was added to ethyl acetate (0.3 mL), and 4N hydrochloric acid in ethyl acetate (230 μL) was added thereto, followed by stirring at 50° C. for six hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate twice. The organic layers were combined, and the combined organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (17 mg) was yielded.

Workup

additionwas added
extractionthe mixture was extracted with ethyl acetate twice
dry with materialthe combined organic layer was dried over sodium sulfate
customThe solvent was evaporated under reduced pressure, whereby the title compound (17 mg)
customwas yielded

Sources & evidence

ORD record: ord-c40e9388f3e04a92ae96e077b855114d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501772B2

Reaction notes

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