Hydrochloric Acid → HCID 86759086, compound

HRID 1359034Notes

Reaction equation

[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]([C@@H:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C@@H:19]([C:34](=[O:37])[NH:35][OH:36])[CH2:18]2)=[O:16])[CH2:11][CH2:10]1)=O)(C)(C)C>>[ClH:1].[OH:36][NH:35][C:34]([C@H:19]1[CH2:18][C@H:17]([C:15]([N:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)=[O:16])[CH2:22][CH2:21][N:20]1[S:23]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)(=[O:25])=[O:24])=[O:37]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 54355662HCID 54355662, compound

Product 1

HCID 86759086HCID 86759086, compound

Procedure

Hydrogen chloride gas was bubbled through a cold (0° C.) solution of (2R,4R)-4-[2-hydroxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-piperidine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (420 mg, 0.8 mmol) for 10 minutes. After an additional 20 minutes the mixture was concentrated to provide (2R, 4R)-1-(4-methoxy-benzenesulfonyl)-4-(piperazine-1-carbonyl)-piperidine-2-carboxylic acid hydroxyamide hydrochloride as a colorless solid: Mass spectrum (atmospheric pressure chemical ionization; basic mode) m/z (M+H) 427, 366; 1H NMR (dimethyl sulfoxide-d6, 400 MHz, ppm) δ 10.70 (bd, 1 H, J=2.7 Hz), 9.06 (bs, 2 H), 8.84 (bs, 1 H), 7.70 (dd, 2 H, J=8.9, 2.9 Hz), 7.06 (dd, 2 H, J=8.9, 2.9 Hz); 4.42 (bs, 1 H), 3.80 (s, 3 H), 3.80-3.20 (m, 6 H), 3.04 (m, 4 H), 2.76 (m, 1 H), 1.79 (bd, 1 H, J=13.5 Hz), 1.52 (bd, 1 H, J=12.6 Hz), 1.32 (m, 1 H), 1.14 (m, 1H).

Workup

concentrationAfter an additional 20 minutes the mixture was concentrated

Sources & evidence

ORD record: ord-25b6c33cb6a2426481cc6360b5fb4123
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599890B1

Reaction notes

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