Ethanol → N-hydroxy-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)-butanamide dihydrochloride

HRID 264335Notes

Reaction equation

HRID 264335 reaction equation
C([O:5][NH:6][C:7](=[O:38])[C@H:8]([N:19]([S:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C@H:9]([O:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:10])(C)(C)C.C(O)C.C(Cl)[Cl:43]>>[ClH:43].[ClH:43].[OH:5][NH:6][C:7](=[O:38])[C@H:8]([N:19]([S:27]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)(=[O:29])=[O:28])[CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[C@H:9]([O:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 6344DichloromethaneHCID 86749033N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)butanamide

Product 1

HCID 86749031N-hydroxy-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)-butanamide dihydrochloride

Conditions

Temperature
-10 °C

Procedure

N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)butanamide (1.3 g, 2.4 mmol) is dissolved in methylene chloride (50 mL) containing ethanol (0.14 mL, 2.4 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 20 minutes. The reaction is sealed, allowed to slowly warm to room temperature, and stirred for two days. The solvent is reduced to 1/3 the volume by evaporation and the residue is triturated with ether. The mixture is filtered, the filter cake is removed and dried in vacuo to provide N-hydroxy-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3(R)-(3-picolyloxy)-butanamide dihydrochloride as a white solid; [α]D25 =+35.26° (c=5.58, DMSO).

Workup

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled through for 20 minutes
  2. customThe reaction is sealed
  3. temperatureto slowly warm to room temperature
  4. customby evaporation
  5. customthe residue is triturated with ether
  6. filtrationThe mixture is filtered
  7. customthe filter cake is removed
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ca30f1b017e14b95a0bee3115602049a
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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