Lithium hydroxide, monohydrate → N-((6-Chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycine

HRID 1868627Notes

Reaction equation

HRID 1868627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7](=[O:17])[C:6]([C:18]([NH:20][CH2:21][C:22]([O:24]C)=[O:23])=[O:19])=[C:5]2[OH:26].O.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)[C:7](=[O:17])[C:6]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])=[C:5]2[OH:26]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67100135HCID 67100135, compound

Product 1

HCID 54719609N-((6-Chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl N-((6-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-2H-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (0.684 g, 1.79 mmol, 1.0 eq.) was suspended in water (10.0 mL) and treated with lithium hydroxide monohydrate (0.227 g, 5.40 mmol). After 30 minutes at ambient temperature, the resulting homogeneous mixture was quenched with 1N HCl solution to pH=2. The white solid that precipitated upon acidification was collected by vacuum filtration and washed with 1:1 H2O/acetone (2×2.0 mL). The product was dried under vacuum at 80° C. for 24 hours to give the title compound in quantitative yield. MS m/e=366.0 (M+H)+. Calculated for C17H16ClNO6 365.07.

Workup

  1. customthe resulting homogeneous mixture was quenched with 1N HCl solution to pH=2
  2. customThe white solid that precipitated upon acidification
  3. filtrationwas collected by vacuum filtration
  4. washwashed with 1:1 H2O/acetone (2×2.0 mL)
  5. customThe product was dried under vacuum at 80° C. for 24 hours

Sources & evidence

ORD record
ord-188d0fd50bcc464a9ac4decaeb8dd955
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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