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

HRID 1716322Notes

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

Participants

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

washwashed sequentially with water and saturated NaCl solution
dry with materialThe organic phase was then dried over anhydrous Na2SO4
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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