Acetyl chloride → 3-(4-Benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxa-diazole

HRID 2075947노트

반응식

HRID 2075947 반응식
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]([NH:15][OH:16])=[NH:14])=[C:11]([I:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](N(CC)CC)[CH3:23].C(Cl)(=O)C>O1CCCC1>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][C:12]([C:13]2[N:14]=[C:22]([CH3:23])[O:16][N:15]=2)=[C:11]([I:21])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178492429HCID 178492429, 화합물

생성물 1

HCID 508988613-(4-Benzyloxy-2-iodo-5-methoxyphenyl)-5-methyl-[1,2,4]oxa-diazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 4-benzyloxy-N-hydroxy-2-iodo-5-methoxy-benzamidine (reference example 3-1) (35 g), triethylamine (31 mL) and tetrahydrofuran (31 mL) was added acetyl chloride (8.2 mL) under ice-bath cooling. The mixture was stirred at the same temperature for 1 hour. Insoluble materials were removed by filtration. To the filtrate was added tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 89 mL). After stirring at the same temperature for 2 hours, water and ethylacetate were added to the mixture. The separated organic layer was washed with 1 mol/L hydrochloric acid, a 1 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with methanol to give the title compound (31.5 g).

후처리

  1. temperaturecooling
  2. customInsoluble materials were removed by filtration
  3. additionTo the filtrate was added tetrabutylammonium fluoride (1 mol/L tetrahydrofuran solution, 89 mL)
  4. stirringAfter stirring at the same temperature for 2 hours
  5. additionwater and ethylacetate were added to the mixture
  6. washThe separated organic layer was washed with 1 mol/L hydrochloric acid
  7. dry with materiala 1 mol/L aqueous solution of sodium hydroxide, an aqueous solution of sodium bicarbonate and brine successively, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with methanol

출처 및 근거

ORD 기록
ord-887054f1f7e24df78e04b7dae8830449
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923462B2

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