Hydrochloric Acid → trans 3-Mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxamide

HRID 21969Notes

Reaction equation

HRID 21969 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]([NH2:18])=[O:17])[NH:8][C:7]1=[O:19])(=O)C.[OH-].[Na+].Cl>C(O)C>[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]([NH2:18])=[O:17])[NH:8][C:7]1=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86747204trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

Product 1

HCID 86747205trans 3-Mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide (0.16 g, 0.56 mmol) is dissolved in ethanol (5.0 mL). An aqueous solution of 1N sodium hydroxide (0.60 mL, 0.60 mmol) is added, and the reaction is stirred for 1 hour. The reaction is acidified with 1N hydrochloric acid to a pH of about 3, 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 (Na2SO4), and the solvent is evaporated to give trans 3-mercaptomethyl-2-oxo-1-azacyclodecane-10-carboxamide, m.p. 185°-192° C.

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 (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f61d6cfb4770496da0610fe231ef78df
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

Loading…