HCID 86621628, compound → HCID 68442728, compound

HRID 2246980Notes

Reaction equation

HRID 2246980 reaction equation
CON(C)[C:4](=[O:48])[CH2:5][CH2:6][C@H:7]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C@@H:10]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]3[O:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:27]=3[CH:37]=2)[CH2:9][N:8]1[S:38]([C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1)(=[O:40])=[O:39].[CH3:50][Mg]Br>>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]2[C@@H:10]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][C:26]4[O:31][CH2:30][CH2:29][N:28]([CH2:32][CH2:33][CH2:34][O:35][CH3:36])[C:27]=4[CH:37]=3)[CH2:9][N:8]([S:38]([C:41]3[CH:42]=[CH:43][C:44]([CH3:47])=[CH:45][CH:46]=3)(=[O:40])=[O:39])[C@@H:7]([CH2:6][CH2:5][C:4](=[O:48])[CH3:50])[CH2:12]2)=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 86621628HCID 86621628, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68442728HCID 68442728, compound

Procedure

Similar to example 29b, 1.68 g of N-methoxy-3-[(2S,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-N-methyl-propionamide in the presence of methyl magnesium bromide are used to afford the title compound after flash chromatography (SiO2 60 F) as a colourless oil. Rf=0.23 (EtOAc-heptane 1:1); Rt=5.25.

Sources & evidence

ORD record
ord-d6e00588f40343258f88c78e31b86520
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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