Hydroxylamine → HCID 11855596, compound

HRID 736761Notes

Reaction equation

HRID 736761 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][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:16][CH:15]=2)(=[O:13])=[O:12])[CH:6]([C:33]([OH:35])=O)[CH2:5]1.[NH2:36][OH:37]>>[OH:37][NH:36][C:33]([CH:6]1[CH:7]([NH:10][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])[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5]1)=[O:35]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 68819523HCID 68819523, compound

Product 1

HCID 11855596HCID 11855596, compound

Procedure

According to the procedure of Example 24, Step 3, 0.4 g (0.8 mmol) of 1-(2-hydroxy-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid and hydroxylamine afforded a ˜2:1 mixture of cis- and trans-1-(2-hydroxy-ethyl)-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid hydroxyamide as an amorphous white solid (0.040 g, 9.7%) after purification using reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column eluting an acetonitrile:water gradient. MS: 515 (M+H)+.

Workup

  1. customafforded
  2. customafter purification
  3. washeluting an acetonitrile

Sources & evidence

ORD record
ord-a77b9836ad194b27901fc332ac27a973
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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