Hydrochloric Acid → HCID 86635423, compound

HRID 599465Notes

Reaction equation

HRID 599465 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:30][CH2:31][O:32][C:33](=[O:35])[CH3:34])([S:14][C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:36]>O1CCOCC1>[ClH:36].[C:26]([C:17]1[CH:16]=[C:15]([S:14][C:11]2([CH2:30][CH2:31][O:32][C:33](=[O:35])[CH3:34])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]=1[OH:25])([CH3:27])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866354224-(2-Acetoxy-ethyl)-4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86635423HCID 86635423, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4-(2-acetoxy-ethyl)-4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester (Ex. 1b, 420 mg) was added 5 mL of 4 N HCl in dioxane. The mixture was stirred for 3 h and then concentrated under reduced pressure. The resulting solid was washed with Ethyl acetate/hexanes (1:3, 20 mL) and dried under high vacuum to afford acetic acid 2-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidin-4-yl]-ethyl ester hydrochloride as a white solid (370 mg, 100%). ESI/CI-MS m/z 408 ([M+H]+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe resulting solid was washed with Ethyl acetate/hexanes (1:3, 20 mL)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-d4a97b5b14c442d9a2bfaacbdd7a6bf5
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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