2-Methyl-2-(oxan-4-yl)propanoic acid → N-{2-[(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]-ethyl}-2-(tetrahydro-pyran-4-yl)-isobutyramide

HRID 2246947Notes

Reaction equation

HRID 2246947 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@H:11]([CH2:42][CH2:43][NH2:44])[CH2:10]2)=[CH:5][CH:4]=1.[CH3:45][C:46]([CH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1)([CH3:50])[C:47](O)=[O:48]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:33])=[O:34])[C@H:11]([CH2:42][CH2:43][NH:44][C:47](=[O:48])[C:46]([CH:51]3[CH2:52][CH2:53][O:54][CH2:55][CH2:56]3)([CH3:50])[CH3:45])[CH2:10]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 668885952-Methyl-2-(oxan-4-yl)propanoic acidHCID 684410362-[(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]-ethylamine

Product 1

HCID 68442966N-{2-[(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]-ethyl}-2-(tetrahydro-pyran-4-yl)-isobutyramide

Procedure

According to general procedure D, 100 mg of 2-[(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]-ethylamine (from example 44b) are reacted with 2-methyl-2-(tetrahydro-pyran-4-yl)-propionic acid [16386-97-3] to afford the title compound as a yellow oil. Rf=0.40 (dichlormethane-methanol-25% ammonia conc. 200:20:1); Rt=3.87.

Sources & evidence

ORD record
ord-32414dffddd148f0b0443c49f5f0c031
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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