Trifluoroacetic acid → HCID 57983520, compound

HRID 1868742Notes

Reaction equation

HRID 1868742 reaction equation
[Cl: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][CH:3]=1.C(O)(C(F)(F)F)=O>>[Cl: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][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099829HCID 67099829, compound

Product 1

HCID 57983520HCID 57983520, compoundYield 61.8%

Procedure

The mixture of 1,1-dimethylethyl N-((7-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (2.23 g, 5 mmol) in TFA (8 mL, 108 mmol) was stirred at room temperature for 20 minutes. The majority of the TFA was removed in vacuo and then water was added. The resulting precipitate was filtered and washed with water to give the desired product as a white solid (1.13 g). MS (m/e)=366.1 (M+H)+. Calculated for C17H16ClNO6 365.07.

Workup

  1. customThe majority of the TFA was removed in vacuo
  2. additionwater was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-e61e0825b64a44b1852a6f9d1984a352
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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