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

HRID 1063871노트

반응식

HRID 1063871 반응식
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

참가 물질

4

반응물 1

HCID 22277851HCID 22277851, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

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

후처리

  1. customevaporated to dryness

출처 및 근거

ORD 기록
ord-981a46114f4f42069dc61846e4588891
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967220B2

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