Hydrochloric Acid → HCID 22644841, compound

HRID 1976436Notes

Reaction equation

HRID 1976436 reaction equation
Cl.[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH3:40])[CH:17]([C:22]2[CH:39]=[CH:38][C:25]([O:26][CH2:27][CH2:28][CH2:29][NH:30]C(=O)OC(C)(C)C)=[CH:24][CH:23]=2)[C:18]([NH:20][OH:21])=[O:19])(=[O:15])=[O:14])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5]>ClCCl>[NH2:30][CH2:29][CH2:28][CH2:27][O:26][C:25]1[CH:38]=[CH:39][C:22]([CH:17]([N:16]([S:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:2][C:3]#[C:4][CH3:5])=[CH:12][CH:11]=2)(=[O:15])=[O:14])[CH3:40])[C:18]([NH:20][OH:21])=[O:19])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22644903HCID 22644903, compound

Product 1

HCID 22644841HCID 22644841, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was bubbled through a solution of 0.371 g (0.661 mmol) of tert-butyl 3-{4-[1-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-2-(hydroxyamino)-2-oxoethyl]phenoxy}propylcarbamate (from Example 187) dissolved in 5 mL of dichloromethane for 5 minutes. The reaction was stoppered at let sit at room temperature for 1 h and then the solvent was evaporated. The residue was triturated with ether, filtered and dried in vacuo to give 0.314 g of 2-[4-(3-aminopropoxy)phenyl]-2-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-N-hydroxyacetamide as a white solid. Electrospray Mass Spec 462.2 (M+H)+

Workup

  1. customthe solvent was evaporated
  2. customThe residue was triturated with ether
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1652b708902e41028a3844d27ca87020
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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