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

HRID 5399Notes

Reaction equation

HRID 5399 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.[ClH:26]>C(O)C>[ClH:26].[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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-degasded 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-azacyclodecan-10-yl]-carbonyl]-amino}-pyridine hydrochloride, MS: M+1=322.

Workup

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

Sources & evidence

ORD record
ord-039d993767fd48bca5979ee161469481
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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