Sodium Hydroxide → (3R)-6-carboxy-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

HRID 5416Notes

Reaction equation

HRID 5416 reaction equation
C[O:2][C:3]([CH:5]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][S:10][CH2:9][C@@H:8]([C:18]([O:20]C)=[O:19])[NH:7][C:6]1=[O:22])=[O:4].[OH-].[Na+]>CO>[C:3]([CH:5]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][S:10][CH2:9][C@@H:8]([C:18]([OH:20])=[O:19])[NH:7][C:6]1=[O:22])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54302673HCID 54302673, compound

Product 1

HCID 54274042(3R)-6-carboxy-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (3R)-6-methoxycarbonyl-5oxo-1-thia-4-azacyclotridecane-3-carboxylate (2.39 g, 7.21 mmol) is suspended in methanol (75 ml) and 1N sodium hydroxide (22.0 ml, 22.0 mmol) is added. The mixture is stirred for 4 hours at room temperature. The solvent is evaporated and the residue is dissolved in water (150 ml). The aqueous solution is adjusted to pH 1 by addition of 1N hydrochloric acid and extracted with ethyl acetate (3×100 ml). The combined extracts are washed with brine (1×100 ml), dried (MgSO4) and the solvent is evaporated to give (3R)-6-carboxy-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid, m.p. 167°-170° C.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in water (150 ml)
  3. additionThe aqueous solution is adjusted to pH 1 by addition of 1N hydrochloric acid
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined extracts are washed with brine (1×100 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d95927d178064a35970f180e99ed80b8
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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