Trifluoroacetic acid → HCID 57983425, compound

HRID 1868712Notes

Reaction equation

HRID 1868712 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[C:5]([CH3:15])([CH3:14])[C:4](=[O:16])[C:3]=1[C:17]([NH:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[O:18].C(O)(C(F)(F)F)=O>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][CH3:13])[CH:10]=2)[C:5]([CH3:14])([CH3:15])[C:4](=[O:16])[C:3]=1[C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099740HCID 67099740, compound

Product 1

HCID 57983425HCID 57983425, compoundYield 97.2%

Procedure

A solution of 1,1-dimethylethyl N-((4-hydroxy-1,1-dimethyl-6-(methylthio)-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.180 g, 0.460 mmol) in TFA (0.0342 mL, 0.460 mmol) was stirred at 25° C. for 10 minutes. The solution was concentrated, azeotroped in DCM (2×300 mL), and dried in vacuo to give the title compound (0.150 g). MS m/e=336 (M+H)+. Calculated for C16H17NO5S 335.08.

Workup

  1. concentrationThe solution was concentrated
  2. customazeotroped in DCM (2×300 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-fdbb66c90b4946549c3e4d37f6ad850f
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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