Sodium Hydroxide → HCID 59184940, compound

HRID 1943315Notes

Reaction equation

HRID 1943315 reaction equation
[O:1]=[C:2]([C@@:18]1([OH:59])[CH2:35][C@H:34]([O:36][C@@H:37]2[O:51][C@@H:50]([CH3:52])[C@H:40]3[O:41][C@H:42]4[N:47]([C@H:39]3[CH2:38]2)[CH2:46][CH2:45][O:44][C@@H:43]4[O:48][CH3:49])[C:33]2[C:20](=[C:21]([OH:58])[C:22]3[C:23](=[O:57])[C:24]4[C:29]([C:30](=[O:54])[C:31]=3[C:32]=2[OH:53])=[C:28]([O:55][CH3:56])[CH:27]=[CH:26][CH:25]=4)[CH2:19]1)[CH2:3][O:4][C:5]1([O:11][CH2:12][C:13]([O:15]CC)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[OH-].[Na+]>O.C(O)(=O)C>[O:1]=[C:2]([C@@:18]1([OH:59])[CH2:35][C@H:34]([O:36][C@@H:37]2[O:51][C@@H:50]([CH3:52])[C@H:40]3[O:41][C@H:42]4[N:47]([C@H:39]3[CH2:38]2)[CH2:46][CH2:45][O:44][C@@H:43]4[O:48][CH3:49])[C:33]2[C:20](=[C:21]([OH:58])[C:22]3[C:23](=[O:57])[C:24]4[C:29]([C:30](=[O:54])[C:31]=3[C:32]=2[OH:53])=[C:28]([O:55][CH3:56])[CH:27]=[CH:26][CH:25]=4)[CH2:19]1)[CH2:3][O:4][C:5]1([O:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59184897HCID 59184897, compound

Product 1

HCID 59184940HCID 59184940, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
5 °C

Procedure

To 30 mg of 45, 5 mL of in 01N NaOH was added. The suspension was cooled at 5° C. and stirred under argon for 3 hours. The aqueous solution was brought to pH≅8 with 10% acetic acid water solution and extracted with dichloromethane (2×10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, the solvent removed under vacuum and the residue purified by flash chromatography (DCM/MeOH 90:10) to give 5 mg (y=8% 2 steps) of the acid intermediate 46 as a red solid. MS (ESI): 798 [M+H]+. Retention time=3.94 min. Method 2

Workup

  1. extractionextracted with dichloromethane (2×10 mL)
  2. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under vacuum
  5. customthe residue purified by flash chromatography (DCM/MeOH 90:10)

Sources & evidence

ORD record
ord-0fd3388dea9a49069f0406841321940f
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

Loading…