Hydrochloric Acid → methyl 4-[(1S)-1-[[(3R)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]amino]ethyl]benzoate hydrochloride

HRID 2205306Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C@H:16]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][N:17]2C(OC(C)(C)C)=O)=[O:15])[CH3:12])=[CH:7][CH:6]=1)=[O:4].O1CCOCC1.[ClH:39]>>[ClH:39].[CH2:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:25][C@H:16]([C:14]([NH:13][C@H:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)[CH3:12])=[O:15])[NH:17]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 131735812tert-butyl (3R)-3-[[(1S)-1-(4-methoxycarbonylphenyl)ethyl]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate

Product 1

HCID 118876958methyl 4-[(1S)-1-[[(3R)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]amino]ethyl]benzoate hydrochlorideYield 100%

Procedure

Dissolve tert-butyl (3R)-3-[[(1S)-1-(4-methoxycarbonylphenyl)ethyl]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate (5.5 g, 12.5 mmol) in a 4 M solution of hydrogen chloride in 1,4-dioxane (30 mL, 120 mmol). Stir the mixture overnight at room temperature, and then concentrate the mixture under reduced pressure to furnish the title compound as a white solid (4.70 g, 100% yield). Mass spectrum (m/z): 339 ([M+H]+), 677 ([2M+H]+), 699 ([2M+Na]+).

Workup

concentrationconcentrate the mixture under reduced pressure

Sources & evidence

ORD record: ord-7fd919c65e21473981cef5e6370261ff
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371289B2

Reaction notes

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