Hydrochloric Acid → HCID 44350054, compound

HRID 21991Notes

Reaction equation

HRID 21991 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-66222cdaa12647648a4d3d5aef4d11b2
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

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