HCID 90741792, compound → HCID 68843005, compound

HRID 2110593Notes

Reaction equation

HRID 2110593 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5](=[O:25])[CH:4]=1>CO.[OH-].[Na+]>[CH3:16][CH:15]([CH3:17])[CH2:14][CH2:13][C:6]1([O:18][CH2:19][C:20]([OH:22])=[O:21])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:2])[CH2:4][C:5]1=[O:25]

Participants

4

Reactant 1

HCID 90741792HCID 90741792, compound

Product 1

HCID 68843005HCID 68843005, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of Example 40A (30 mg, 0.087 mmol) in methanol (0.2 mL) and 1 N NaOH (0.2 mL) was stirred at 25° C. for 16 hours. The methanol was evaporated. The resulted solution was acidified with 1N HCl to pH 3, extracted with ethyl acetate, dried (Na2SO4), and filtered. The filtrate was concentrated in vacuo to afforded the title compound (24 mg, 91%) and used for the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.35-0.49 (m, 1H,) 0.69 (dd, J=13.05, 6.43 Hz, 6H), 0.77-0.96 (m, 1H), 1.24-1.36 (m, 1H), 1.83-1.94 (m, 1H), 2.04-2.22 (m, 1H), 3.18 (d, 1H), 3.67 (d, J=15.44 Hz, 1H), 5.76 (s, 1H), 7.45-7.55 (m, 1H), 7.59-7.73 (m, 2H), 7.90 (d, J=7.72 Hz, 1H), 11.83-12.71 (br. s, 1H); MS (ESI) m/z 304.9 (M+H)+.

Workup

  1. customThe methanol was evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-87cdcad79e5041a9b820983ad39ae3bd
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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