1,1-Dimethylethyl N-((6''-chloro-4''-hydroxy-5,5-dimethyl-2''-oxo-dispiro[1,3-dioxane-2,1'-cyclohexane-4',1''-naphthalen]-3''-yl)carbonyl)glycinate → N-((6'-Chloro-4'-hydroxy-2',4-dioxo-spiro[cyclohexane-1,1'-naphthalen]-3'-yl)carbonyl)glycine

HRID 2078237Notes

Reaction equation

HRID 2078237 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:16][CH2:15][C:14]3(OCC(C)(C)C[O:17]3)[CH2:13][CH2:12]1)[C:7](=[O:24])[C:6]([C:25]([NH:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[O:26])=[C:5]2[OH:36]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:7](=[O:24])[C:6]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[C:5]2[OH:36]

Participants

3

Reactant 1

HCID 670997051,1-Dimethylethyl N-((6''-chloro-4''-hydroxy-5,5-dimethyl-2''-oxo-dispiro[1,3-dioxane-2,1'-cyclohexane-4',1''-naphthalen]-3''-yl)carbonyl)glycinate

Product 1

HCID 57983380N-((6'-Chloro-4'-hydroxy-2',4-dioxo-spiro[cyclohexane-1,1'-naphthalen]-3'-yl)carbonyl)glycineYield 83.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((6″-chloro-4″-hydroxy-5,5-dimethyl-2″-oxo-dispiro[1,3-dioxane-2,1′-cyclohexane-4′,1″-naphthalen]-3″-yl)carbonyl)glycinate (18 mg, 35 μmol) in 1 mL TFA was stirred at room temperature for 30 minutes, M+1=378. The mixture was concentrated in vacuo, and dried under high vacuum to give 11 mg of the product as an off-white solid. MS (m/z)=378 (M+H)+. Calculated for C18H16ClNO6 377.07.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-3902ef00c4cf4e348ea0294e97e2fa43
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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