Hydrochloric Acid → 2-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carboxylic acid

HRID 508168노트

반응식

HRID 508168 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:18]=[O:19])=[C:11]([CH2:13][O:14][CH2:15][O:16][CH3:17])[N:12]=2)=[CH:4][CH:3]=1.[O:20]1CCOCC1.[OH-].[Na+].Cl>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([C:18]([OH:20])=[O:19])=[C:11]([CH2:13][O:14][CH2:15][O:16][CH3:17])[N:12]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 582843772-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carbaldehyde

생성물 1

HCID 582843362-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carboxylic acid

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 962Water용매2회

실험 절차

556 mg (2.25 mmol) of the compound from Example 41A and 14.7 ml of dioxane are added to a suspension of 802 mg (4.72 mmol) of silver(I) nitrate in 2 ml of water. A solution of 193 mg (4.84 mmol) of sodium hydroxide in 7.8 ml of water is then added slowly. The mixture is stirred at RT for 3 h. The mixture is then filtered through Celite, which is washed with warm water. The filtrate obtained is acidified by addition of 1 N hydrochloric acid and extracted three times with in each case 20 ml of diethyl ether. The combined organic phases are dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

후처리

  1. filtrationThe mixture is then filtered through Celite, which
  2. washis washed with warm water
  3. customThe filtrate obtained
  4. extractionextracted three times with in each case 20 ml of diethyl ether
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. customthe solvent is removed on a rotary evaporator
  7. customThe residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

출처 및 근거

ORD 기록
ord-2ea36c54df0948bda397cf370e38abdd
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09095582B2

반응 노트

불러오는 중…