1,1-Dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)-L-alaninate → N-((6-Chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)-L-alanine

HRID 2078174Notes

Reaction equation

HRID 2078174 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:23]([O:25]C(C)(C)C)=[O:24])[CH3:22])=[O:19])=[C:5]2[OH:30]>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@H:21]([C:23]([OH:25])=[O:24])[CH3:22])=[O:19])=[C:5]2[OH:30]

Participants

3

Reactant 1

HCID 670992391,1-Dimethylethyl N-((6-chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)-L-alaninate

Product 1

HCID 57983442N-((6-Chloro-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)-L-alanineYield 84%

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)-L-alaninate (525 mg, 1204 μmol) was dissolved in TFA for 30 minutes before it was concentrated, precipitated with hexanes, washed with hexanes, and dried in a vacuum oven to give the title compound (384 mg) as a white solid. MS (m/z)=380 (M+H)+. Calculated for C18H18ClNO6 379.08.

Workup

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

Sources & evidence

ORD record
ord-467ce3984b644a6a8a4e4bd27e1e394c
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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