Hydrochloric Acid → HCID 57983479, compound

HRID 2078316Notes

Reaction equation

HRID 2078316 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][C@@H:18]([C:20]([O:22]C)=[O:21])[CH3:19])=[O:16])=[C:5]2[OH:24].[OH-].[Na+].O.Cl>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][C@@H:18]([C:20]([OH:22])=[O:21])[CH3:19])=[O:16])=[C:5]2[OH:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67099736HCID 67099736, compound

Product 1

HCID 57983479HCID 57983479, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl N-((6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-D-alaninate (75 mg, 213 μmol) was dissolved in THF (2132 μL). 5N NaOH in water (2132 μL, 10660 μmol) was added at ambient temperature, and the reaction was stirred for 3 hours. The reaction mixture was acidified with 3N HCl, diluted with 50 mL of EtOAc, added to a separatory funnel, washed 2 times with 20 mL of brine (saturated, aqueous), separated, dried over Na2SO4, and concentrated to give the title compound as a white amorphous solid. MS m/e 338 (M+H)+. Calculated for C16H16ClNO5 337.07.

Workup

  1. additionadded to a separatory funnel
  2. washwashed 2 times with 20 mL of brine (saturated, aqueous)
  3. customseparated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b3fbe0e3bb746da8047fd4f7a1c536d
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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