Hydroxylamine → HCID 86585704, compound

HRID 1008274Notes

Reaction equation

HRID 1008274 reaction equation
CC1(C)[O:6][C:5](=O)[CH:4]([CH:8]([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[C:20]([NH2:22])=[O:21])=[O:14])[CH2:9][CH2:10][CH2:11][CH3:12])[O:3]1.[NH2:24][OH:25]>O1CCOCC1>[OH:25][NH:24][C:5](=[O:6])[C@@H:4]([OH:3])[C@@H:8]([CH2:9][CH2:10][CH2:11][CH3:12])[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([NH2:22])=[O:21])=[O:14]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86585702HCID 86585702, compound

Product 1

HCID 86585704HCID 86585704, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 1-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-aminocarbonylpyrrolidin-1-ylcarbonyl)pentane C-3 in dioxane was treated with 50% aqueous hydroxylamine for 4 h. The reaction mixture was then purified by preparative reverse-phase (C18) HPLC to afford N-hydroxy-3-(R)-n-butyl-3-[2-(S)-aminocarbonylpyrrolidin-1-ylcarbonyl)-2-(S)-hydroxypropionamide C-4.

Workup

  1. customThe reaction mixture was then purified by preparative reverse-phase (C18) HPLC

Sources & evidence

ORD record
ord-340bef68d7284053992d23150de58a0b
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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