Hydroxylamine → HCID 86607885, compound

HRID 736778Notes

Reaction equation

HRID 736778 reaction equation
[CH3:1][N:2]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:3]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[CH:4]1[C:10](O)=[O:11].CCN=C=NCCCN(C)C.C1C=CC2[N:53]([OH:54])N=NC=2C=1.NO>CN(C=O)C.C(OCC)(=O)C>[OH:54][NH:53][C:10]([C@@H:4]1[C@H:3]([N:2]([CH3:1])[S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:20][CH:21]=2)(=[O:14])=[O:15])[C@@H:8]2[CH2:9][C@H:5]1[CH2:6][CH2:7]2)=[O:11]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68821219HCID 68821219, compound

Product 1

HCID 86607885HCID 86607885, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{methyl-[4-(quinolin-2-ylmethoxy)-benzenesulfonyl]-amino}-bicyclo[2.2.1]heptane-2-carboxylic acid (125 mg, 0.268 mmol) in DMF (1 mL) were added EDCI (103 mg, 0.536 mmol), HOBT (72.5 mg, 0.536 mmol) and hydroxylamine (50% in water, 82 μL, 1.34 mmol) at room temperature. The mixture was stirred for 20 h, diluted with ethyl acetate (5 mL), and washed with water (3×3 mL) and brine (3 mL). The organic layer was concentrated and the residue was purified by RP-HPLC to give (1R,2S,3R,4S)-N-hydroxy-3-(methyl{[4-(quinolin-2-ylmethoxy)phenyl]sulfonyl}amino)bicyclo[2.2.1]heptane-2-carboxamide (50% yield). MS (ESI) [M+H] 482.2

Workup

  1. washwashed with water (3×3 mL) and brine (3 mL)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-80791da9c6bf4c55891f017bd48f30da
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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