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

HRID 1063871ノート

反応式

HRID 1063871 の反応式
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

参加物

4

反応物 1

HCID 22277851HCID 22277851、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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

後処理

  1. customevaporated to dryness

出典と根拠

ORDレコード
ord-981a46114f4f42069dc61846e4588891
出典データセット
uspto-grants-2005_11
特許番号
US06967220B2

反応ノート

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