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

HRID 5397Notes

Reaction equation

HRID 5397 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-b118b628f60746c29335fc3e59194550
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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