Hydrochloric Acid → (R)-piperidine-4-carboxylic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester hydrochloride

HRID 915289Notes

Reaction equation

HRID 915289 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][O:18][C:19](=[O:46])[N:20]([C:43](=[O:45])[CH3:44])[CH2:21][C@@H:22]2[O:26][C:25](=[O:27])[N:24]([C:28]3[CH:33]=[CH:32][C:31]([CH:34]4[CH2:39][CH2:38][S:37](=[O:41])(=[O:40])[CH2:36][CH2:35]4)=[C:30]([F:42])[CH:29]=3)[CH2:23]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.[ClH:55].CCOCC>O1CCCC1.O1CCOCC1>[ClH:55].[C:43]([N:20]([CH2:21][C@@H:22]1[O:26][C:25](=[O:27])[N:24]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]3[CH2:39][CH2:38][S:37](=[O:40])(=[O:41])[CH2:36][CH2:35]3)=[C:30]([F:42])[CH:29]=2)[CH2:23]1)[C:19]([O:18][CH2:17][O:16][C:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15])=[O:46])(=[O:45])[CH3:44]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7519AnisoleHCID 11331321HCID 11331321, compound

Product 1

HCID 11753752(R)-piperidine-4-carboxylic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-Piperidine-1,4-dicarboxylic acid 4-[(acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl] ester 1-tert-butyl ester (17) (588.5 mg, 0.88 mmol) and anisole (0.9 mL) are diluted with tetrahydrofuran (17 mL). Hydrochloric acid in dioxane (4 M, 6.6 mL) is added dropwise and the resultant mixture is stirred at RT overnight. Ether is added dropwise to the mixture while stirring, resulting in the formation of a solid. The solid is collected via filtration, rinsed with ether, and dried under vacuum to give the title compound in quantitative yield (530.8 mg, 0.88 mmol) 1H NMR (400 MHz, CD3OD): δ 7.51 (dd, 1H), 7.36 (t, 1H), 7.26 (dd, 1H), 5.92 (s, 2H), 4.15-422 (m, 2H), 4.05 (dd, 1H), 3.81 (dd, 1H), 3.36-3.43 (m, 4H), 3.23 (tt, 1H), 3.05-3.14 (m, 5H), 2.90 (tt, 1H), 2.52 (s, 3H), 2.35 (q, 2H), 2.13-2.26 (m, 4H), 1.92-2.00 (m, 2H). MS-APCI (m/z+): 570.

Workup

  1. customresulting in the formation of a solid
  2. filtrationThe solid is collected via filtration
  3. washrinsed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f7b1e37846b546ecb042adc90e883f8d
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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