Ethanol → HCID 22856281, compound

HRID 264299Notes

Reaction equation

HRID 264299 reaction equation
C([O:5][NH:6][C:7](=[O:39])[C@H:8]([N:20]([S:28]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:19])[CH2:15][N:16]([CH3:18])[CH3:17])(C)(C)C.C(O)C.[Cl:43]C(Cl)C>>[ClH:43].[OH:5][NH:6][C:7](=[O:39])[C@H:8]([N:20]([S:28]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:19])[CH2:15][N:16]([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 63651,1-DichloroethaneHCID 22856310HCID 22856310, compound

Product 1

HCID 22856281HCID 22856281, compound

Conditions

Temperature
-10 °C

Procedure

N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-[(N,N-dimethylglycyl)amino]hexanamide (2.17 g, 3.86 mmol) is dissolved in dichloroethane (12 mL) containing ethanol (0.22 mL, 3.86 mmol), and the reaction is cooled to -10° C. Hydrochloric acid gas is bubbled through this solution for 30 minutes. The reaction is sealed, warmed to room temperature and stirred for 2 days. The solvent is reduced to 1/2 volume by evaporating solvent, and triturated with ether. The resulting solid is removed and dried in vacuo to provide N-hydroxy-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-[(N,N-dimethylglycyl)amino]hexanamide hydrochloride, m.p. 105°-108° C.

Workup

  1. customHydrochloric acid gas is bubbled through this solution for 30 minutes
  2. customThe reaction is sealed
  3. temperaturewarmed to room temperature
  4. customby evaporating solvent
  5. customtriturated with ether
  6. customThe resulting solid is removed
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6294547257f0431081cea52ba1f0e9eb
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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