Cyclobutanol → HCID 59314411, compound

HRID 1047906Notes

Reaction equation

HRID 1047906 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:27]=[C:26]([F:28])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[OH:29])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH:30]1(O)[CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:27]=[C:26]([F:28])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[O:29][CH:30]2[CH2:33][CH2:32][CH2:31]2)=[O:17])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 76218CyclobutanolHCID 59314215HCID 59314215, compound

Product 1

HCID 59314411HCID 59314411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[(4-fluoro-1-hydroxynaphthalene-2-carbonyl)amino]indan-2-carboxylic acid ethyl ester (303) (197 mg, 0.5 mmol) and 3,3-dimethyl-1,2,5-thiadiazolidine-5 triphenylphosphine-1,1-dioxide (example 307, 245 mg, 0.6 mmol, 1.2 eq) in DCM (6 mL) is treated with cyclobutanol (44 mg, 0.6 mmol, 1.2 eq) and stirred at RT for 6 days. The crude reaction mixture is purified by flash chromatography (100 g silica gel, 100% DCM) to give colorless oil. (120 mg, 54%)

Workup

  1. customThe crude reaction mixture
  2. customis purified by flash chromatography (100 g silica gel, 100% DCM)
  3. customto give colorless oil

Sources & evidence

ORD record
ord-7e5488b76947476383d52c8e8b3a9c79
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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