Hydroxylamine → HCID 86607882, compound

HRID 736747Notes

Reaction equation

[CH3:1][N:2]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([CH3:32])[CH:23]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:3]1[CH2:7][O:6][CH2:5][CH:4]1[C:8]([OH:10])=O.[NH2:33][OH:34]>>[OH:34][NH:33][C:8]([C@H:4]1[C@@H:3]([N:2]([CH3:1])[S:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:24]([CH3:32])[CH:23]=3)=[CH:18][CH:19]=2)(=[O:12])=[O:13])[CH2:7][O:6][CH2:5]1)=[O:10]

Participants

Reactant 2

HCID 787Hydroxylamine

HCID 68818793HCID 68818793, compound

Product 1

HCID 86607882HCID 86607882, compoundYield 21%

Procedure

According to the procedure of Example 24, Step 3, 4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-furan-3-carboxylic acid (0.160 g, 0.35 mmol) and hydroxylamine gave (3S,4R)-4-{methyl-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl]-amino}-tetrahydro-furan-3-carboxylic acid hydroxyamide as an amorphous white solid (0.035 g, 21%) after purification using Biotage Flash 40S chromatography, eluting with 5% methanol in ethyl acetate. MS: 472 (M+H)+

Sources & evidence

ORD record: ord-e97496039dd44595ad1603cfbc4afe89
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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