Cornforth reagent → HCID 68625259, compound

HRID 1819967Notes

Reaction equation

[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][O:23][C:24](=[O:26])[CH3:25].[CH2:27]([C:29]([C:47]1[S:51][C:50]([S:52]([NH2:55])(=[O:54])=[O:53])=[C:49]([CH3:56])[CH:48]=1)([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH:40]([OH:45])[C:41]([CH3:44])([CH3:43])[CH3:42])=[C:34]([CH3:46])[CH:33]=1)[CH2:30][CH3:31])[CH3:28]>>[CH3:22][O:23][C:24](=[O:26])[CH3:25].[CH3:44][C:41]([CH3:42])([CH3:43])[C:40](=[O:45])[CH2:39][CH2:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]([C:47]2[S:51][C:50]([S:52]([NH2:55])(=[O:54])=[O:53])=[C:49]([CH3:56])[CH:48]=2)([CH2:30][CH3:31])[CH2:27][CH3:28])=[CH:33][C:34]=1[CH3:46]

Participants

Reactant 2

HCID 2724130Cornforth reagent

HCID 68625813HCID 68625813, compound

Product 1

HCID 68625259HCID 68625259, compoundYield 96%

Procedure

Using the pyridinium dichromate oxidation analogous to Example 139C, (5-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-sulfonylamine)-acetic acid methyl ester gives the title compound (96%). 1H NMR (CDCl3) δ 6.96, 7.02 (m, 3H), 6.59 (s, 1H), 5.22 (t, 1H), 3.83 (d, 1H, J=5.7 Hz), 3.65 (s, 3H), 2.82 (t, 2H), 2.72 (t, 2H), 2.40 (s, 3H), 2.27 (s, 3H), 2.07 (m, 4H), 1.10 (s, 9H), 0.68 (t, 6H);

Sources & evidence

ORD record: ord-84edaf142ac140fcbd1b6a7f47904ded
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601850B2

Reaction notes

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