Ethanol → Butanamide, N-hydroxy-2-(((4-methoxyphenyl)sulfonyl)(3-pyridinylmethyl)amino)-3-methyl-, hydrochloride (1:1), (2R)-

HRID 2209664Notes

Reaction equation

HRID 2209664 reaction equation
C([O:5][NH:6][C:7](=[O:31])[C@H:8]([N:12]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:9]([CH3:11])[CH3:10])(C)(C)C.C(O)C.[Cl:35]C(Cl)C>>[ClH:35].[OH:5][NH:6][C:7](=[O:31])[C@H:8]([N:12]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:9]([CH3:11])[CH3:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 63651,1-DichloroethaneHCID 10671218N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide

Product 1

HCID 9888897Butanamide, N-hydroxy-2-(((4-methoxyphenyl)sulfonyl)(3-pyridinylmethyl)amino)-3-methyl-, hydrochloride (1:1), (2R)-

Conditions

Temperature
-10 °C

Procedure

N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide (4.1 g, 9.13 mmol) is dissolved in dichloroethane (150 mL) containing ethanol (0.53 ml, 9.13 mmol) in a round bottom flask, and the reaction is cooled to -10° C. Hydrochloric acid gas (from a lecture bottle) is bubbled through for 30 minutes. The reaction is sealed, allowed to slowly warm to room temperature, and stirred for 2 days. The solvent is reduced to 1/3 volume by evaporation and triturated with ether. The mixture is filtered, filter cake removed, and dried in vacuo to provide N-hydroxy-2(R)-[[4-methoxybenzenesulfonyl]-(3-picolyl)amino]-3-methylbutanamide hydrochloride as a white solid, m.p. 169°-170° C. (dec), and having the following structure: ##STR12##

Workup

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled through for 30 minutes
  2. customThe reaction is sealed
  3. temperatureto slowly warm to room temperature
  4. customThe solvent is reduced to 1/3 volume by evaporation
  5. customtriturated with ether
  6. filtrationThe mixture is filtered
  7. filtrationfilter cake
  8. customremoved
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ddcb5870dd9641d6bab86b1d4e777546
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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