Ammonia → N-Methyl-O-{3-cyclohexyl-2-[4-(pyrid-2-yl-methoxy)phenyl]propionyl}-hydroxylamine

HRID 1708503Notes

Reaction equation

HRID 1708503 reaction equation
ON(C)[C:3](=[O:26])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:14][CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.N.[CH3:29][NH:30][OH:31].CN(C)O>>[CH3:29][NH:30][O:31][C:3](=[O:26])[CH:4]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:17]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 11647MethylhydroxylamineHCID 27970DimethylhydroxylamineHCID 152303333-Cyclohexyl-2-[4-(pyrid-2-yl-methoxy)phenyl]propionic acid N-hydroxy-N-methyl-amide

Product 1

HCID 18958986N-Methyl-O-{3-cyclohexyl-2-[4-(pyrid-2-yl-methoxy)phenyl]propionyl}-hydroxylamine

Procedure

The above material was obtained as a side product of Example 11. 1H NMR (DMSO-d6, 300 MHz) δ 0.9 (m, 2H), 1.1 (m, 4H), 1.63 (m, 6H), 1.81 (m, 1H), 2.6 (d, J=6Hz, 3H), 3.65 (t, J=7Hz, 1H), 5.17 (s, 2H), 7.0 (d, J=7Hz, 2H), 7.23 (d, J=7Hz, 2H), 7.35 (m, 1H), 7.5 (d, J=8Hz, 1H), 7.83 (dt, J=8Hz, 2Hz, 1H), 7.9 (q, J=6Hz, 1H), 8.6 (m, 1H). IR (CDCl3): 3245, 1735, 1610 cm-1. MS (DCI/NH3) m/e 369 (M+H)+. The above material was also obtained according to the procedures described in Example 17 substituting N-methylhydroxyl-amine for N,N-dimethylhydroxylamine.

Workup

  1. customThe above material was also obtained

Sources & evidence

ORD record
ord-ec85c4536097459aaa9bb4fd4fe9d978
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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