Sodium Hydroxide → HCID 10814133, compound

HRID 583703Notes

Reaction equation

HRID 583703 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:10]2[CH:33]=[CH:32][C:13]([C:14]([NH:16][CH2:17][C@H:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:19]([OH:21])=[O:20])=[O:15])=[CH:12][CH:11]=2)[N:3]=1.[OH-].[Na+]>O.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]2[CH:33]=[CH:32][C:13]([C:14]([NH:16][CH2:17][C@H:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:19]([OH:21])=[O:20])=[O:15])=[CH:12][CH:11]=2)[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86752455HCID 86752455, compound

Product 1

HCID 10814133HCID 10814133, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Alkyne 29-6 (60 mg, 0.13 mmol), was suspended in 1.3 mL H2O, 1N NaOH was added until the mixture was homogeneous, 10% Pd/C (12 mg) was added, and an H2 balloon was applied. After 16 h the reaction was filtered, concentrated, and purified by flash chromatography (silica, 12:10:1:1 EtOAc/EtOH/NH4OH/H2O) providing 29-7 as a white solid.

Workup

  1. filtrationAfter 16 h the reaction was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (silica, 12:10:1:1 EtOAc/EtOH/NH4OH/H2O)

Sources & evidence

ORD record
ord-5d764918559d41629e6b584a7b396ea9
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

Loading…