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4-Methoxyphenol → 3-[4-(4-Methoxy-phenoxy)-benzenesulfonyl]-1-trityloxy-azepan-2-one

HRID 1716322
Notes
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Reaction equation

HRID 1716322 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]2=[O:38])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.CCOC(C)=O>[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH:11]3[CH2:17][CH2:16][CH2:15][CH2:14][N:13]([O:18][C:19]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:12]3=[O:38])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:43][CH:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 685136933-(4-Fluoro-benzenesulfonyl)-1-trityloxy-azepan-2-one

Product 1

HCID 685163403-[4-(4-Methoxy-phenoxy)-benzenesulfonyl]-1-trityloxy-azepan-2-one

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 31374
Dimethylacetamide
Solvent

Conditions

Temperature
100 °C

Procedure

A Mixture of 3-(4-fluoro-benzenesulfonyl)-1-trityloxy-azepan-2-one prepared from step F (18.9 mg, 0.0357 mmol), 4-methoxy-phenol (19.2 mg, 0.154 mmol) and K2CO3 (38.1 mg, 0.275 mmol) in anhydrous DMA (1.5 mL) was stirred and heated at 100° C. for overnight. The reaction mixture was diluted with EtOAc and washed sequentially with water and saturated NaCl solution. The organic phase was then dried over anhydrous Na2SO4 and concentrated under reduced pressure to gave a crude material, which was then purified by a column chromatography (0˜25% EtOAc in hexane). MS: 656.5 (M+Na)+.

Workup

  1. washwashed sequentially with water and saturated NaCl solution
  2. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37e6fe15b55f43ab91300e09decc8e94
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803793B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes