Potassium Hydroxide → [3-(3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenoxy)-propyl]-carbamic acid tert-butyl ester

HRID 574060Notes

Reaction equation

HRID 574060 reaction equation
[OH-].[K+].[CH3:3][C:4]1([CH3:30])[CH2:8][O:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:29])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]3[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=3)=[CH:11][CH:10]=2)=[N:5]1.[C:31]([O:35][C:36](=[O:42])[NH:37][CH2:38][CH2:39][CH2:40]Br)([CH3:34])([CH3:33])[CH3:32]>CS(C)=O>[C:31]([O:35][C:36](=[O:42])[NH:37][CH2:38][CH2:39][CH2:40][O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3[O:7][CH2:8][C:4]([CH3:30])([CH3:3])[N:5]=3)=[CH:14][CH:13]=2)([OH:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:17]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 599879993-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol

Product 1

HCID 68670565[3-(3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenoxy)-propyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of powdered KOH (45 mg, 0.8 mM) in anhydrous DMSO (2.5 mL) at room temperature was added 3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol (2, 150 mg, 0.4 mM) and (3-Bromo-propyl)-carbamic acid tert-butyl ester (96 mg, 0.4 mM). The reaction mixture was stirred at room temperature for 3 h. Then the reaction mixture was extracted with ethyl acetate (3×25 mL) and the combined extract was dried over anhydrous Mg2SO4. The residue obtained on evaporation of the solvent was purified by silica gel chromatography using hexane/EtOAc (1:1) as an eluent. Evaporation of the solvent gave 3. Yield: >220 mg (quantitative yield). Mass: 531 (MH+).

Workup

  1. extractionThen the reaction mixture was extracted with ethyl acetate (3×25 mL)
  2. extractionthe combined extract
  3. dry with materialwas dried over anhydrous Mg2SO4
  4. customThe residue obtained on evaporation of the solvent
  5. customwas purified by silica gel chromatography
  6. customEvaporation of the solvent
  7. customgave 3

Sources & evidence

ORD record
ord-51448e41f9b74dcf8daeef20f359a339
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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