Sodium Hydroxide → 5-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acid

HRID 1911316노트

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HRID 1911316 반응식
[CH:1]([C:3]1[S:7][C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)=[O:2].[OH-:21].[Na+]>C(O)C.O.[N+]([O-])([O-])=O.[Ag+]>[CH3:18][C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6]2[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][CH:5]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])[CH3:19]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 28065298Tert-butyl 4-(5-formylthiophen-2-yl)piperazine-1-carboxylate

생성물 1

HCID 543134535-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}thiophene-2-carboxylic acid수율 71%

시약·촉매·용매 3

HCID 24470Silver Nitrate촉매HCID 702Ethanol용매HCID 962Water용매

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온도
65 °C

실험 절차

A solution of tert-butyl 4-(5-formylthien-2-yl)piperazine-1-carboxylate (2.51 g, 8.50 mmol) in ethanol (85 ml) was added in one portion to a solution of silver (I) nitrate (10.0 g, 58.8 mmol) and sodium hydroxide (4.83 g, 120.6 mmol) in water (85 ml). This mixture was stirred and heated at 65° C. for 22 h. The mixture was cooled by the addition of ice and then filtered to remove silver salts. The filtrate was carefully evaporated to remove the ethanol and the resulting aqueous solution was filtered again through a glass-fibre pad to remove tarry material. The filtrate was then diluted with water to a total volume of 400 ml and then acidified to pH 5 with acetic acid. The precipitate was filtered off, washed with water and then dried in a vacuum oven at 45° C. overnight to give 5-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]thiophene-2-carboxylic acid (1.88 g, 71%).

후처리

  1. temperatureThe mixture was cooled by the addition of ice
  2. filtrationfiltered
  3. customto remove silver salts
  4. customThe filtrate was carefully evaporated
  5. customto remove the ethanol
  6. filtrationthe resulting aqueous solution was filtered again through a glass-fibre pad
  7. customto remove tarry material
  8. additionThe filtrate was then diluted with water to a total volume of 400 ml
  9. filtrationThe precipitate was filtered off
  10. washwashed with water
  11. customdried in a vacuum oven at 45° C. overnight

출처 및 근거

ORD 기록
ord-5d15b5d95073431c8f20077d38fdb5ca
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604022B2

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