Hydrochloric Acid → HCID 44350054, compound

HRID 5418Notes

Reaction equation

HRID 5418 reaction equation
C([S:4][CH2:5][CH:6]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:19]([O:21]C)=[O:20])[NH:8][C:7]1=[O:23])(=O)C.O.[OH-].[Li+].Cl>>[SH:4][CH2:5][CH:6]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:19]([OH:21])=[O:20])[NH:8][C:7]1=[O:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54177672Methyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

Product 1

HCID 44350054HCID 44350054, compound

Procedure

Methyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate (Isomer B) (0.16 g, 0.44 mmol) is partially dissolved in nitrogen degassed tetrahydrofuran (10 ml) and water (5 ml). Lithium hydroxide monohydrate (0.056 g, 1.33 mmol) is added and the mixture is stirred at room temperature for 3 hours. The mixture is poured into 1N hydrochloric acid and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with brine (1×50 ml), dried (Na2SO4) and the solvent is evaporated to give (3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (Isomer B), m.p. 169°-173° C.; the more active NEP inhibiting isomer.

Workup

  1. customdegassed tetrahydrofuran (10 ml) and water (5 ml)
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe combined organic layers are washed with brine (1×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-8a5922e693b148e3b13ed802c0393b83
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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