Hydroxylamine → HCID 86585704, compound

HRID 1008282Notes

Reaction equation

HRID 1008282 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]([OH:22])=O)=[O:14])[CH2:9][CH2:10][CH2:11][CH3:12])[O:3]1.CCN(C(C)C)C(C)C.CN(C([O:40][N:41]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C[N:60]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.NO>O1CCOCC1>[OH:40][NH:41][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]([NH2:60])=[O:22])=[O:14]

Participants

7

Reactant 5

HCID 787HydroxylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86585703HCID 86585703, compound

Product 1

HCID 86585704HCID 86585704, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To 1-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-carboxy-pyrrolidin-1-ylcarbonyl)pentane F-6 (50 mg) in dioxane (1 mL) was added an amine RNH2 (1 equivalent), DIEA (2.5 equivalents) and HATU or PyBOP (1 equivalent) and the solution stirred for 4 h. The reaction was then cooled to 0° C., 50% aqueous hydroxylamine was added (400 μL), and the solution stirred at 4° C. for 8 hours. The crude reaction mixture was then purified by preparative reverse-phase (C18) HPLC to afford N-hydroxy-3-(R)-n-butyl-3-[2-(S)-aminocarbonylpyrrolidin-1-yl-carbonyl)-2-(S)-hydroxypropionamide F-7.

Workup

  1. stirringthe solution stirred at 4° C. for 8 hours
  2. customThe crude reaction mixture
  3. customwas then purified by preparative reverse-phase (C18) HPLC

Sources & evidence

ORD record
ord-7e63e24285054dc0b254bf127dfa5fed
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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