Hydroxylamine → 2-[{[4-(2,3-Butadienyloxy)phenyl]sulfonyl}(methyl)amino]-N-hydroxy-3-methylbutanamide

HRID 1180545Notes

Reaction equation

HRID 1180545 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C@H:16]([C:20]([OH:22])=O)[CH:17]([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]=[CH2:4].[OH:23][N:24]1C2C=CC=CC=2N=N1.Cl.[CH3:34]N(C)CCCN=C=NCC.CN1CCOCC1.NO>>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH3:34])[CH:16]([CH:17]([CH3:19])[CH3:18])[C:20]([NH:24][OH:23])=[O:22])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]=[CH2:4]

Participants

6

Reactant 5

HCID 787HydroxylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86588656N-{[4-(2,3-Butadienyloxy)phenyl]sulfonyl}valine

Product 1

HCID 101328212-[{[4-(2,3-Butadienyloxy)phenyl]sulfonyl}(methyl)amino]-N-hydroxy-3-methylbutanamideYield 57.2%

Procedure

The procedure of Example 13 was followed using the product from Example 15 (250 mg, 0.74 mmol), 1-hydroxybenzotriazol (119 mg, 0.88 mmol), 1-[3-(dimethylamino)-propyl]-3-ethylcarbodimide hydrochloride (199 mg, 1.04 mmol), N-methylmorpholine (0.122 mmol, 1.11 mmol), and hydroxylamine (0.226 ml, 3.7 mmol) to give 150 mg (57%) of the product.

Sources & evidence

ORD record
ord-0dec10d300d9450fa234bffd65355111
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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