HCID 67099753, compound → HCID 57983406, compound

HRID 2078192Notes

Reaction equation

HRID 2078192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:7](=[O:17])[C:6]([C:18]([NH:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:19])=[C:5]2[OH:29]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:7](=[O:17])[C:6]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])=[C:5]2[OH:29]

Participants

3

Reactant 1

HCID 67099753HCID 67099753, compound

Product 1

HCID 57983406HCID 57983406, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((6′-chloro-4′-hydroxy-2′-oxo-spiro[cyclohexane-1,1′-naphthalen]-3′-yl)carbonyl)glycinate (185 mg, 441 μmol) was dissolved in TFA (2 mL) at ambient temperature for 30 minutes. The reaction mixture was then concentrated, and the product was precipitated with hexanes, filtered, washed with ether, and dried in a vacuum oven to give the title compound (119 mg) as a white solid. MS (m/z)=364 (M+H)+. Calculated for C18H18ClNO5 363.09.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe product was precipitated with hexanes
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-2a57af706ae04a45a75ee4d5b530dbed
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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