Trifluoroacetic acid → HCID 57983552, compound

HRID 2078252Notes

Reaction equation

HRID 2078252 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:16]=1[C:10]1([CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:9](=[O:17])[C:8]([C:18]([NH:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19])=[C:7]2[OH:29].C(O)(C(F)(F)F)=O>O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:16]=1[C:10]1([CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:9](=[O:17])[C:8]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])=[C:7]2[OH:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099943HCID 67099943, compound

Product 1

HCID 57983552HCID 57983552, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask was combined 1,1-dimethylethyl N-((8-fluoro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (1.7 g, 4.2 mmol) and TFA (50 mL). The reaction was stirred for 15 minutes and then concentrated to afford an oil. Water was added, affording a white precipitate that was filtered off and washed with water and ether. The solid was dried under vacuum at 50° C. (1.4 g, 98%). MS m/e=348 (M−1)−. Calculated for C17H16FNO6 349.1.

Workup

  1. customIn a flask was combined
  2. concentrationconcentrated
  3. customto afford an oil
  4. customaffording a white precipitate that
  5. filtrationwas filtered off
  6. washwashed with water and ether
  7. customThe solid was dried under vacuum at 50° C. (1.4 g, 98%)

Sources & evidence

ORD record
ord-ac09d94fd1ee450ab391823ab8238f52
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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