Methanol → HCID 22117500, compound

HRID 1478219Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH:23]([OH:25])[CH3:24])[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[CH3:31]O>>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH:23]([OH:25])[CH3:24])[C:20]([O:22][CH3:31])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 43362173731-37-0

Product 1

HCID 22117500HCID 22117500, compound

Procedure

To a solution of 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxybutanoic acid (5 g, 14.65 mmol) in MeOH (50 mL) was added H2SO4 (0.781 mL, 14.65 mmol). The reaction mixture was stirred at reflux overnight. The resulting mixture was cooled to room temperature and the solvent removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography using a gradient of 0-100% EtOAc in iso-hexane afforded the title compound;

Workup

temperatureat reflux overnight
customthe solvent removed under reduced pressure
customThe crude material was adsorbed onto silica and purification by chromatography

Sources & evidence

ORD record: ord-8f50064827894f7caa41673ecfaaa77f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403810B2

Reaction notes

Loading…