HCID 67099579, compound → HCID 57983560, compound

HRID 2078079Notes

Reaction equation

HRID 2078079 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:17][CH3:18])[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21]>C(O)(C(F)(F)F)=O>[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:17][CH3:18])[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21]

Participants

3

Reactant 1

HCID 67099579HCID 67099579, compound

Product 1

HCID 57983560HCID 57983560, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((4-hydroxy-5-(methyloxy)-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (32 mg, 77 μmol) in 2 mL TFA was stirred at room temperature for 30 minutes, M+1=362, M−1=360. The mixture was concentrated in vacuo, and purified by column chromatography eluting with 0.1:10:100 TFA/MeOH/DCM to give 9 mg of the product as a pale yellow solid. MS (m/z)=362 (M+H)+. Calculated for C18H19NO7 361.12.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by column chromatography
  3. washeluting with 0.1:10:100 TFA/MeOH/DCM

Sources & evidence

ORD record
ord-54894394c3064dddb781867b22e5852b
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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