Hydrochloric Acid → HCID 86664941, compound

HRID 1620390Notes

Reaction equation

HRID 1620390 reaction equation
[ClH:1].[OH:2][NH:3][C:4](=[O:36])[C@@H:5]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9]>C(O)(C)C>[ClH:1].[ClH:1].[OH:2][NH:3][C:4](=[O:36])[C@@H:5]([N:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49854511HCID 49854511, compound

Product 1

HCID 86664941HCID 86664941, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.4 ml (2.0 mmol) of a solution of isopropanolic hydrochloric acid having a concentration of 5-6N is added to a solution of 400 mg (0.8 mmol) of (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)-benzenesulfonylamino]-2-piperidin-1-ylpropionamide (prepared as described in example 8) in 8 ml of isopropanol. The reaction medium is stirred at ambient temperature for 2 h and then filtered. The residue obtained is recrystallized from a 10/1 isopropanol/water mixture, filtered and dried under vacuum. 260 mg (56%) of (S)—N-hydroxy-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropionamide dihydrochloride are obtained in the form of a white solid with a melting point of 188° C.

Workup

  1. filtrationfiltered
  2. customThe residue obtained
  3. customis recrystallized from a 10/1 isopropanol/water mixture
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-776e365234b941c0be6c10167d45364d
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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