Water → HCID 57983561, compound

HRID 1868890Notes

Reaction equation

HRID 1868890 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][C@H:21]([C:24]([O:26]C)=[O:25])[CH2:22][OH:23])=[O:19])=[C:5]2[OH:28].[OH-].[Na+].O>C1COCC1.CCOC(C)=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][C@H:21]([C:24]([OH:26])=[O:25])[CH2:22][OH:23])=[O:19])=[C:5]2[OH:28]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67100020HCID 67100020, compound

Product 1

HCID 57983561HCID 57983561, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl N-((6-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)-L-serinate (180 mg, 439 μmol) was dissolved in THF (4392 μL). NaOH in water (4392 μL, 21961 μmol) was added, and the reaction was stirred at ambient temperature for 3 hours. The pH was adjusted to about 3, and the resulting mixture was diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 20 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (95 mg) after it was precipitated with hexanes, filtered, washed with hexanes, and dried in a vacuum oven. MS m/e=396 (M+H)+. Calculated for C18H18NO7 395.08.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with water
  3. washwashed 2 times with 20 mL of water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29e91d743aa0419a882a97f78a85b6ad
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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