HCID 67100256, compound → HCID 57983375, compound

HRID 2078213Notes

Reaction equation

HRID 2078213 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=2)[C:5]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[C:4](=[O:22])[C:3]=1[C:23]([NH:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[O:24]>C(O)(C(F)(F)F)=O.CCOCC>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:10]=2)[C:5]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[C:4](=[O:22])[C:3]=1[C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24]

Participants

4

Reactant 1

HCID 67100256HCID 67100256, compound

Product 1

HCID 57983375HCID 57983375, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((4′-hydroxy-2′-oxo-6′-phenyl-spiro[cyclopentane-1,1′-naphthalen]-3′-yl)carbonyl)glycinate (115 mg, 257 μmol) was dissolved in TFA (2 mL) at ambient temperature. The reaction was stirred for 30 minutes and was then concentrated to give an oil, dissolved in ether, concentrated again to give an amorphous solid, precipitated with ether, filtered, washed with ether, and dried in a vacuum oven to give the title compound (21 mg) as a white solid. MS (m/z)=392 (M+H)+. Calculated for the C23H21NO5 391.14.

Workup

  1. concentrationwas then concentrated
  2. customto give an oil
  3. concentrationconcentrated again
  4. customto give an amorphous solid
  5. customprecipitated with ether
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8756e05bde4e4c198ecf2db6c31bc20d
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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