Benzyl chloroformate → 2-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

HRID 54084노트

반응식

HRID 54084 반응식
[CH:1]1([C:14]([OH:16])=[O:15])[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>[OH-].[Na+].O.O1CCOCC1>[CH2:21]([O:20][C:18]([N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:1]1[C:14]([OH:16])=[O:15])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 2

HCID 10387Benzyl chloroformateHCID 1458792,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole-1-carboxylic acid

생성물 1

HCID 190319922-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

시약·촉매·용매 3

HCID 962Water용매2회HCID 14798Sodium Hydroxide용매2회HCID 312751,4-Dioxane용매2회

실험 절차

To a solution, cooled in ice, of 3.0 g of 1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid in 7 ml of 2M sodium hydroxide solution, 17 ml of water and 17 ml of dioxan were added in alternating portions 12.5 ml of 2M sodium hydroxide solution and a solution of 3.6 ml of benzyl chloroformate in 9 ml of dioxan. After completion of the additions the mixture was stirred at room temperature overnight and the dioxan-was then removed by evaporation under reduced pressure. The solution obtained was diluted with water, washed twice with diethyl ether, acidified with 25 ml of 1M sulphuric acid and extracted three times with ethyl acetate. The organic extracts were combined, washed twice with water, dried over anhydrous magnesium sulphate and evaporated to give 4.54 g of 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid, MS: m/e 351 [M+H]+, which was used without purification.

후처리

  1. additionwere added
  2. customthe dioxan-was then removed by evaporation under reduced pressure
  3. customThe solution obtained
  4. washwashed twice with diethyl ether
  5. extractionextracted three times with ethyl acetate
  6. washwashed twice with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated

출처 및 근거

ORD 기록
ord-0edde3a643e240ed8791c3430222056f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620987

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