Lithium Hydroxide → HCID 57751788, compound

HRID 2272818Notes

Reaction equation

HRID 2272818 reaction equation
[OH:1][C@@H:2]1[C@H:7]([OH:8])[C@@H:6]([O:9][CH3:10])[C:5]([CH3:12])([CH3:11])[O:4][C@H:3]1[O:13][C:14]1[C:23]([CH3:24])=[C:22]2[C:17]([CH:18]=[C:19]([NH:26][C:27](=[O:36])[C:28]3[CH:33]=[CH:32][C:31](OC)=[CH:30][CH:29]=3)[C:20](=[O:25])[O:21]2)=[CH:16][CH:15]=1.[OH-:37].[Li+].[Cl-].[NH4+:40].C1[CH2:45][O:44]CC1.C[OH:47].O>>[CH3:10][O:9][C@H:6]1[C:5]([CH3:12])([CH3:11])[O:4][C@@H:3]([O:13][C:14]2[C:23]([CH3:24])=[C:22]3[C:17]([CH:18]=[C:19]([NH:26][C:27](=[O:36])[C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([N+:40]([O-:47])=[O:37])[CH:29]=4)[C:20](=[O:25])[O:21]3)=[CH:16][CH:15]=2)[C@@H:2]2[O:1][C:45](=[O:44])[O:8][C@H:7]12

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 21892291Methanol tetrahydrofuran waterHCID 24851148HCID 24851148, compound

Product 1

HCID 57751788HCID 57751788, compoundYield 47%

Procedure

To a solution of substrate 11 (68 mg, 0.130 mmol) in THF:MeOH:H2O (1.5:1:1 mL) was added lithium hydroxide (27 mg, 0.65 mmol) at room temperature. The reaction mixture was stirred for 1 hour and neutralized with saturated ammonium chloride solution, extracted with ethyl acetate (3×5 mL), washed with brine. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica using dichloromethane and methanol (96:4) as eluent to give diastereomers 16a (30 mg, 47%) and 16b (20 mg, 31%), both as white amorphous solids.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washwashed with brine
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-c311070c21004692b07965371583cf4b
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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