HCID 22277851, compound → Phenol, 4-[4-[(hydroxyamino)methyl]-2,6-diiodophenoxy]-

HRID 1063871Notes

Reaction equation

HRID 1063871 reaction equation
C(OC([O:8][N:9]([CH2:17][C:18]1[CH:23]=[C:22]([I:24])[C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[C:20]([I:33])[CH:19]=1)C(=O)OC(C)(C)C)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[OH:8][NH:9][CH2:17][C:18]1[CH:19]=[C:20]([I:33])[C:21]([O:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[C:22]([I:24])[CH:23]=1

Participants

4

Reactant 1

HCID 22277851HCID 22277851, compound

Product 1

HCID 22277849Phenol, 4-[4-[(hydroxyamino)methyl]-2,6-diiodophenoxy]-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution containing tert-butyl N-(tert-butoxycarbonyloxy)-N-[3,5-diiodo-4-(4-hydroxyphenoxy)benzyl]carbamate (150 mg, 0.21 mmol) in 4 ml of 30% TFA in CH2Cl2 was stirred for 2 h and then evaporated to dryness to afford 4-(4-hydroxyaminomethyl-2,6-diiodophenoxy)phenol (M+1=484). This residue was then treated with triethylamine (0.5 ml) and the mixed anhydride (0.5 ml) [made from formic acid and acetic anhydride (1:2 v/v) at 50° C. for 1 h] in 2 ml of CH2Cl2 for 0.5 h. All volatiles were removed and the residue dissolved in methanol then treated with 10% NaOH for 0.5 h. This was diluted with ethyl acetate and water and adjusted to pH of 6. The layers were separated and the organic extract was evaporated in vacuo. Purification by preparative HPLC afforded the title compound (27 mg, 25%) as an off white solid. 1H NMR (400 MHz, CD3OD): δ 8.38, 8.18* (s, 1H); 7.89*, 7.86 (s, 2H); 6.69 (d, j=8.8 Hz, 2H); 6.55 (d, j=8.8 Hz, 2H),; 4.67, 4.63* (s, 2H). M+1=512. *: minor rotamer

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-981a46114f4f42069dc61846e4588891
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

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