Hydrochloric Acid → 3-(N-[[trans 3-mercaptomethyl-2-oxo-1-azacylodecan-10-yl]-carbonyl]-amino)-pyridine hydrochloride

HRID 21971Notes

Reaction equation

HRID 21971 reaction equation
C([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:17])[NH:8][C:7]1=[O:25])(=O)C.[OH-].[Na+].[ClH:28]>C(O)C>[ClH:28].[SH:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:17])[NH:8][C:7]1=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867472063-(N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-amino)-pyridine

Product 1

HCID 867472073-(N-[[trans 3-mercaptomethyl-2-oxo-1-azacylodecan-10-yl]-carbonyl]-amino)-pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-amino)-pyridine (0.040 g, 0.11 mmol) is dissolved in ethanol (1.0 mL). An aqueous solution of nitrogen-degassed 1N sodium hydroxide (0.33 mL, 0.33 mmol) is added, and the reaction is stirred for 90 minutes. The reaction is quenched with 1N hydrochloric acid (0.33 mL, 0.33 mmol), and the solvent is evaporated. The residue is partitioned between ethyl acetate and water, and the aqueous layer is extracted several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The residue is dissolved in methylene chloride (5.0 mL), and anhydrous hydrochloric acid gas is bubbled through the reaction for 5 minutes. The solvent is evaporated to give 3-(N-[[trans 3-mercaptomethyl-2-oxo-1-azacylodecan-10-yl]-carbonyl]-amino)-pyridine hydrochloride, MS: M+1=322.

Workup

  1. additionis added
  2. customthe solvent is evaporated
  3. customThe residue is partitioned between ethyl acetate and water
  4. extractionthe aqueous layer is extracted several times with ethyl acetate
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe solvent is evaporated
  7. dissolutionThe residue is dissolved in methylene chloride (5.0 mL)
  8. customanhydrous hydrochloric acid gas is bubbled through the reaction for 5 minutes
  9. customThe solvent is evaporated

Sources & evidence

ORD record
ord-7d558e7cc69e4f5bb357ac42d1fbb5f3
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

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