Trifluoroacetic acid → HCID 57983465, compound

HRID 1868888Notes

Reaction equation

HRID 1868888 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:17])[C:3]=1[C:18]([NH:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19].C(O)(C(F)(F)F)=O>>[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:17])[C:3]=1[C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099828HCID 67099828, compound

Product 1

HCID 57983465HCID 57983465, compoundYield 0.1%

Procedure

1,1-Dimethylethyl N-((4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (270 mg, 697 mmol) was reacted with TFA (2 mL) for 30 minutes and then concentrated, precipitated with hexanes, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (193 mg) as a white solid. MS m/e=332 (M+H)+. Calculated for C17H17NO6 331.11.

Workup

  1. concentrationconcentrated
  2. customprecipitated with hexanes
  3. filtrationfiltered
  4. washwashed with hexanes
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-7a1b4a6587b0418ea53fa06de95dcb32
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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