Trifluoroacetic acid → 5-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide

HRID 11569노트

반응식

HRID 11569 반응식
[CH3:1][CH:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(OC(=O)[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35]([C:37]1[S:38][C:39]([CH2:42][NH2:43])=[CH:40][CH:41]=1)=[O:36])(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35]([C:37]1[S:38][C:39]([CH2:42][NH:43][C:4](=[O:6])[CH2:3][CH:2]([CH3:1])[CH2:7][CH3:8])=[CH:40][CH:41]=1)=[O:36]

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 77553-Methylpentanoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 69655378{2-[(5-Aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

생성물 1

HCID 100204565-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide수율 59.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 33.43 mg (0.288 mmol) 3-methylpentanoic acid in 1 ml THF were added 46.67 mg (0.288 mmol) 1,1′-carbonyldiimidazol. After 1 h at rt 100 mg (0.288 mmol) {2-[(5-aminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester were added and the reaction mixture was stirred for 3 h at rt. 1.7 ml trifluoroacetic acid were added and after 2 h at rt sat. aqueous NaHCO3 was added carefully and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/heptane 6:4) to yield 59.3 mg (0.171 mmol) 5-[(3-Methyl-pentanoylamino)-methyl]-thiophene-2-carboxylic acid (2-amino-phenyl)-amide; exact MW [M+H] calc'd: 346.16; MW found [M+H]: 346.4.

후처리

  1. additionwas added carefully
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-fde35acb794e44f89d09261016546ce8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098247B2

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