Hydroxylamine → HCID 56932957, compound

HRID 1019670Notes

Reaction equation

HRID 1019670 reaction equation
CO[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH2:15])[CH2:8][C:7]=2[CH:6]=1)=[O:4].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([S:26](Cl)(=[O:28])=[O:27])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].[OH:30][NH2:31].[OH-].[K+]>ClCCl>[OH:30][NH:31][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][CH:9]([NH:15][S:26]([C:20]3[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=3)(=[O:28])=[O:27])[CH2:8][C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 58055425HCID 58055425, compound

Product 1

HCID 56932957HCID 56932957, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in two steps according to Scheme 6 by (1) treating amine VII with 3,4-dimethoxybenzenesulfonyl chloride and TEA in dichloromethane, and (2) treating the ester intermediate with aqueous HONH2 and KOH. MS: calc'd (MH+) 407, exp (MH+) 407.5. 1H NMR (CD3OD, 400 MHz), 7.51 (dd, 1H, J1=8.4 Hz, J2=2.0 Hz), 7.46 (d, 1H, J=8.0 Hz), 7.42 (d, 1H, J=1.6 Hz), 7.35 (s, 1H), 7.11 (m, 2H), 3.92 (s, 3H), 3.88 (s, 3H), 3.55 (m, 1H), 2.95 (m, 2H), 2.82 (m, 1H), 2.69 (m, 1H), 1.95 (m, 1H) 1.73 (m, 1H).

Sources & evidence

ORD record
ord-da7efd7ae1b34ab2af2a0340c20c6127
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

Loading…