Hydrochloric Acid → HCID 23513831, compound

HRID 278342Notes

Reaction equation

HRID 278342 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][C:16]2([C:33]([NH:35][OH:36])=[O:34])[CH2:21][CH2:20][N:19]([C:22]([C:24]3([CH3:32])[CH2:29][O:28]C(C)(C)[O:26][CH2:25]3)=[O:23])[CH2:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].Cl>C1COCC1.CCOC(C)=O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][C:16]2([C:33]([NH:35][OH:36])=[O:34])[CH2:17][CH2:18][N:19]([C:22](=[O:23])[C:24]([CH2:25][OH:26])([CH3:32])[CH2:29][OH:28])[CH2:20][CH2:21]2)(=[O:13])=[O:14])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23513792HCID 23513792, compound

Product 1

HCID 23513831HCID 23513831, compoundYield 694.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-({[4-(2-Butynyloxy)phenyl]sulfonyl}methyl)-N-hydroxy-1-[(2,2,5-trimethyl-1,3-dioxan-5-yl)carbonyl]-4-piperidinecarboxamide (0.106 g, 0.2 mmol) and 2 mL of 1N HCl in 2 mL of THF was stirred at room temperature for 4 h. The reaction was diluted with EtOAc, washed with H2O, saturated NaHCO3, brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was triturated with ether to provide 0.67 g (71%) of the desired product as an off white solid. Electrospray Mass Spec: 483.2 (M+H)+

Workup

  1. washwashed with H2O, saturated NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-21d8c140fcb045efaa1657f7dfffa8a0
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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