Hydrochloric Acid → (3S,4R)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid

HRID 736754Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)=[O:4].Cl>O1CCOCC1>[CH3:33][C:25]1[CH:24]=[C:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([S:12]([NH:11][C@@H:10]3[CH2:9][CH2:8][NH:7][CH2:6][C@@H:5]3[C:3]([OH:4])=[O:2])(=[O:13])=[O:14])=[CH:16][CH:17]=2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 0.3 g (0.525 mmol) of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (Example 28, Step 6) in 1,4-dioxane (4 mL) was added concentrated HCl (4 mL). The reaction was heated to 60° C. for 19 h. The solvent was then removed in vacuo to give (3S,4R)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid as the hydrochloride salt (0.210 g, 72.4%). MS: 457 (M+H)+

Workup

customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-8fb06095d346449fb13d984e37414280
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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