Ammonium Hydroxide → HCID 50939112, compound

HRID 1971739Notes

Reaction equation

HRID 1971739 reaction equation
[C:1]([N:5]1[CH2:43][CH2:42][CH2:41][CH2:40][C:8]2[C:9]([C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([N:20]5[CH:24]=[C:23]([CH2:25][C@H:26]6[CH2:30][O:29]C(C)(C)[O:27]6)[N:22]=[N:21]5)[C:16]([O:33][CH3:34])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:44])([CH3:4])([CH3:3])[CH3:2].[NH4+].[OH-]>C(O)(=O)C>[C:1]([N:5]1[CH2:43][CH2:42][CH2:41][CH2:40][C:8]2[C:9]([C:35]3[S:36][CH:37]=[CH:38][CH:39]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([N:20]5[CH:24]=[C:23]([CH2:25][C@H:26]([OH:27])[CH2:30][OH:29])[N:22]=[N:21]5)[C:16]([O:33][CH3:34])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:44])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 58124824HCID 58124824, compound

Product 1

HCID 50939112HCID 50939112, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 20e (30 mg) was dissolved in 2 ml of 80% acetic acid and stirred for 2 days at RT. The mixture was diluted with ice-water and neutralized by addition of conc. NH4OH. The product was extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated, and the remainder purified by chromatography over silica gel, (using a gradient of heptane/acetone as eluent), to provide 12 mg of 20f.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe remainder purified by chromatography over silica gel

Sources & evidence

ORD record
ord-f0bf9604c8a94cd696a8845353a367b7
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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