Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate → tert-butyl N-[[3-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methyl]-N-(2-hydroxyethyl)carbamate

HRID 219896Notes

Reaction equation

HRID 219896 reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6](C(OC)=O)=[C:5](F)[CH:4]=1.C(C1C=C(C=CC=1)[CH2:21][N:22]([CH2:30][CH2:31][OH:32])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])#N>>[NH2:1]/[C:2](=[N:14]\[OH:15])/[C:3]1[CH:4]=[C:5]([CH:6]=[CH:11][CH:12]=1)[CH2:21][N:22]([CH2:30][CH2:31][OH:32])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27]

Participants

3

Reactant 2

HCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoateHCID 86645651tert-Butyl 3-cyanobenzyl(2-hydroxyethyl)carbamate

Product 1

HCID 59495768tert-butyl N-[[3-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methyl]-N-(2-hydroxyethyl)carbamate

Procedure

Title compound was prepared following procedure described for Intermediate 1 step 2 but starting from tert-Butyl 3-cyanobenzyl(2-hydroxyethyl)carbamate obtained from step 2 (6 g, 0.0217 mol) (RT for 12 h). Reaction mixture was concentrated under reduced pressure and purified by column chromatography using silica gel and chloroform/methanol as a eluent to afford the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.60 (s, 1H), 7.52-7.53 (m, 2H), 7.31-7.34 (m, 1H), 7.19-7.20 (m, 1H), 5.76 (s, 1H), 4.65-4.68 (m, 1H), 4.42 (s, 2H), 3.42-3.47 (m, 2H), 3.13-3.16 (m, 2H), 1.33-1.41 (m, 9H). LC/MS (Method A): 310.0 (M+H)+. HPLC (Method B) Rt 4.57 min (Purity: 94.1%).

Workup

  1. customTitle compound was prepared following procedure
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-99d4c005d5bc4da3bf2fb0251a64783e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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