Triacetoxyperiodinane → HCID 57681030, compound

HRID 244143Notes

Reaction equation

HRID 244143 reaction equation
[OH:1][CH:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[N+:14]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=1[NH:4][CH2:3][C:2](=[O:1])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:9]([OH:11])=[O:10])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57680910HCID 57680910, compound

Product 1

HCID 57681030HCID 57681030, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A DCM (50 mL) suspension of 4-[(2-hydroxy-2-phenylethyl)amino]-3-nitrobenzoic acid (1.0 g, 3.3 mmol) was treated with Dess-Martin periodinane reagent (1.5 g, 3.5 mmol) at rt in one lot. The reaction mixture was stirred at rt for 2 h. The solid was filtered off and washed with DCM to afford the title compound as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 12.97 (br, 1H), 9.08 (t, J=4.4 Hz, 1H), 8.67 (d, J=2.0 Hz, 1H), 8.14 (d, J=8.0 Hz, 2H), 8.01 (dd, J=1.6 Hz, 8.8 Hz, 1H), 7.72 (t, J=7.6 Hz, 1H), 7.61 (t, J=7.6 Hz, 2H), 7.23 (d, J=8.8 Hz, 1H), 5.14 (d, J=4.8 Hz, 2H). MS (ES+): m/z 301.1 (40) [MH+]; HPLC: tR=3.10 min (OpenLynx, polar—5 min).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with DCM

Sources & evidence

ORD record
ord-28b8504b4d114157b7d0a2daa707ef54
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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