{[4-(4-Iodo-phenoxy)-benzenesulphonyl]-carboxymethyl-amino}-acetic acid → {[4-(4-Iodo-phenoxy)-benzenesulphonyl]-hydroxycarbamoylmethyl-amino}-acetic acid

HRID 37749Notes

Reaction equation

HRID 37749 reaction equation
F[C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:22][C:23]([OH:25])=[O:24])[CH2:17][C:18](=[O:21])[NH:19][OH:20])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[I:28]C1C=CC(OC2C=CC(S(N(CC(O)=O)CC(O)=O)(=O)=O)=CC=2)=CC=1>>[I:28][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]([CH2:22][C:23]([OH:25])=[O:24])[CH2:17][C:18](=[O:21])[NH:19][OH:20])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66916708{[4-(4-Iodo-phenoxy)-benzenesulphonyl]-carboxymethyl-amino}-acetic acidHCID 86655169{[4-(4-Fluoro-phenoxy)-benzenesulphonyl]-hydroxycarbamoylmethyl-amino}-acetic acid

Product 1

HCID 75034189{[4-(4-Iodo-phenoxy)-benzenesulphonyl]-hydroxycarbamoylmethyl-amino}-acetic acid

Procedure

Compound 6e was prepared following the procedure described for 6b with reagent quantities adapted to the amount of starting material 5e (500 mg, 1.02 mmol). Yield: 305 mg, 0.60 mmol, 59%. 1H NMR (D2O): δ 7.72 (d, 3J=8.2 Hz, 2H, ArH), 7.52 (d, 3J=8.8 Hz, 2H, ArH), 7.03 (d, 3J=8.8 Hz, 2H, ArH), 4.01 (s, 4H, CH2COOH). ESI-MS calcd for C16H15IN2O7S 505.97 [M-H]−, obsd 507.0.

Sources & evidence

ORD record
ord-f4423d5a7d39437e92063b41a8a65f53
Source dataset
uspto-grants-2013_09
Patent number
US08524194B2

Reaction notes

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