1,1-Dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)-2-methylalaninate → HCID 57983563, compound

HRID 1868764Notes

Reaction equation

HRID 1868764 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:21]([CH3:30])([C:23]([O:25]C(C)(C)C)=[O:24])[CH3:22])=[O:19])=[C:5]2[OH:31]>C(O)(C(F)(F)F)=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:21]([CH3:22])([C:23]([OH:25])=[O:24])[CH3:30])=[O:19])=[C:5]2[OH:31]

Participants

3

Reactant 1

HCID 670998271,1-Dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)-2-methylalaninate

Product 1

HCID 57983563HCID 57983563, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)-2-methylalaninate (245 mg, 545 μmol) was dissolved in TFA at ambient temperature for 1 hour before it was concentrated, precipitated with hexanes, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (179 mg) as a white solid. MS (m/z)=394 (M+H)+. Calculated for C19H20ClNO6 393.10.

Workup

  1. concentrationwas concentrated
  2. customprecipitated with hexanes
  3. filtrationfiltered
  4. washwashed with hexanes
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8f7a0f512b244851851c2aa313c7e42c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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