1,1'-Carbonyldiimidazole → HCID 69655347, 화합물

HRID 11568

반응식

HRID 11568 반응식
[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:29]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH2:43])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1COCC1>[C:32]([O:31][C:29](=[O:30])[NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][C:14]([C:12]1[S:13][C:9]([CH2:8][N:4]([CH2:1][CH:2]=[CH2:3])[CH2:5][CH:6]=[CH2:7])=[CH:10][CH:11]=1)=[O:16])([CH3:35])([CH3:33])[CH3:34]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 21975913HCID 21975913, 화합물

생성물 1

HCID 69655347HCID 69655347, 화합물수율 84.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2.70 g (11.38 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid in 50 ml THF was added 2.03 g (12.51 mmol) carbonyldiimidazol. After 45 min at rt, 2.48 g (11.95 mmol) mono-boc-ortho-phenylenediamine were added to the reaction mixture, and it was stirred for 3 h at rt. The solvent was evaporated and the residue dissolved in ethyl acetate. The organic phase was washed twice with sat. NaHCO3, once with water and dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/heptane 2:8) to yield 4.10 g (9.59 mmol) {2-[(5-Diallylaminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; exact MW [M+H] calc'd: 428.20; MW found [M+H]: 428.3.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase was washed twice with sat. NaHCO3, once with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-b8e9914bc2ed46f08901e363f3b422c0
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098247B2

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