Hydroxylamine → (3S, 4R)-4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid hydroxyamide

HRID 736741Notes

Reaction equation

HRID 736741 reaction equation
[CH3:1][N:2]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[C:25]([CH3:33])[CH:24]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH:4]1[C:9]([OH:11])=O.[NH2:34][OH:35]>>[OH:35][NH:34][C:9]([C@H:4]1[C@H:3]([N:2]([CH3:1])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7][O:6][CH2:5]1)=[O:11]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 68817278HCID 68817278, compound

Product 1

HCID 86607880(3S, 4R)-4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid hydroxyamideYield 40%

Procedure

According to the procedure of Example 24, Step 3, 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid (0.120 g, 0.255 mmol) and hydroxylamine provided (3S,4R)-4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-pyran-3-carboxylic acid hydroxyamide as an amorphous white solid (0.050 g, 40%) after purification by Biotage Flash 40S chromatography, eluting with 4% methanol in ethyl acetate. MS: 486 (M+H)+.

Sources & evidence

ORD record
ord-69bec64aa09d487da7cda6dd31dfe01e
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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