HCID 67099312, compound → HCID 57983390, compound

HRID 1868664Notes

Reaction equation

HRID 1868664 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[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]=[C:14]([O:17][CH3:18])[CH:15]=2)[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 67099312HCID 67099312, compound

Product 1

HCID 57983390HCID 57983390, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((4-hydroxy-6-(methyloxy)-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (0.66 g, 1.6 mmol) in 3 mL TFA was stirred at room temperature for 30 minutes, M+1=362, M−1=360. The mixture was concentrated and triturated in DCM/heptane (5:10). The solid was filtered, washed with 10 mL DCM/heptane (5:10), and dried under high vacuum to give 0.52 g of the product as a white solid. MS (m/z)=362 (M+H)+. Calculated for C18H19NO7 361.12.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated in DCM/heptane (5:10)
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL DCM/heptane (5:10)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-16617261120a490fbb3c30ff57fb08db
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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