Sodium Hydroxide → HCID 9933755, compound

HRID 257820Notes

Reaction equation

HRID 257820 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([C:30]([O:32]C)=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)[C:13](=[O:34])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:35])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([C:30]([OH:32])=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)[C:13](=[O:34])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:35])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15291262HCID 15291262, compound

Product 1

HCID 9933755HCID 9933755, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step D (22 mg, 0.047 mmol) in MeOH (5 mL) was added 1N NaOH (2 mL). The reaction mixture was stirred 0.5 hours, and was then concentrated in vacuo. The residue was taken up in water and acidified to pH=2 with 1N HCl. Next, the aqueous layer was partitioned with chloroform and extracted 3 times. The combined organic layers were dried (MgSO4), filtered and the filtrate concentrated in vacuo to yield 15 mg (65%) of the title compound (Rf =0.40, hexane/ethyl acetate/acetic acid (75:23.5:1.5)).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customNext, the aqueous layer was partitioned with chloroform
  3. extractionextracted 3 times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-dca2ba11811349e3872cf91966d4464f
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

Loading…