HCID 67099587, compound → HCID 57983467, compound

HRID 1868655Notes

Reaction equation

HRID 1868655 reaction equation
[Br:1][C:2]1[CH:16]=[C:15]2[C:5]([C:6]([OH:29])=[C:7]([C:18]([NH:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19])[C:8](=[O:17])[C:9]32[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][C:3]=1[O:30][CH3:31]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:16]=[C:15]2[C:5]([C:6]([OH:29])=[C:7]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[C:8](=[O:17])[C:9]32[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][C:3]=1[O:30][CH3:31]

Participants

3

Reactant 1

HCID 67099587HCID 67099587, compound

Product 1

HCID 57983467HCID 57983467, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((7-bromo-4-hydroxy-6-(methyloxy)-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (0.27 g, 0.54 mmol) in 3 mL TFA was stirred at room temperature for 30 minutes, M+1=440/442. The mixture was concentrated and triturated in ether (20 mL). The solid was filtered, washed with 10 mL ether and dried under high vacuum to give 0.22 g of the product as a white solid. MS m/e=440/442 (M+H)+. Calculated for C18H18BrNO7 439.03/441.02.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated in ether (20 mL)
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-980d68d115d94eb0acefb6052d64a84e
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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