7-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester → 3-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine-7-sulfonyl)-phenol

HRID 1616894노트

반응식

HRID 1616894 반응식
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:20]=[CH:19][C:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30]CC5C=CC=CC=5)[CH:25]=4)(=[O:23])=[O:22])=[CH:17][C:15]=3[O:16][C:10]=2[CH2:9]1)=O)(C)(C)C>CO.CCOC(C)=O.[Pd]>[CH2:9]1[C:10]2[O:16][C:15]3[CH:17]=[C:18]([S:21]([C:24]4[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=4)(=[O:22])=[O:23])[CH:19]=[CH:20][C:14]=3[C:11]=2[CH2:12][CH2:13][NH:8]1

참가 물질

5

반응물 1

HCID 673238427-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester

생성물 1

HCID 673256153-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine-7-sulfonyl)-phenol

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 7-(3-benzyloxy-benzenesulfonyl)-3,4-dihydro-1H-benzofuro[2,3-c]pyridine-2-carboxylic acid tert-butyl ester (50 mg, 0.1 mmol) in 5 mL methanol and 1 mL EtOAc was added Pd black (10% on carbon, 45 mg, 3.4 mmol). The mixture was kept under hydrogenation at 40 psi overnight and the solvent was evaporated. After filtration, the debenzylated product was taken to the next step without further purification. Removal of N-Boc protecting group with 4N HCl using a general procedure afforded the title product. mp 279-281° C., MS m/z 330 [M+H]+. 1H-NMR (400 MHz, DMSOd6): δ 10.26 (s, 1H), 9.76 (br s, 2H), 8.24 (s, 1H), 7.84 (m, 2H), 7.39 (m, 2H), 7.30 (s, 1H), 7.02 (m, 1H), 4.47 (s, 2H), 3.44 (m, 2H), 2.94 (m, 2H).

후처리

  1. customwas kept under hydrogenation at 40 psi overnight
  2. customthe solvent was evaporated
  3. filtrationAfter filtration
  4. customthe debenzylated product was taken to the next step without further purification
  5. customRemoval of N-Boc protecting group with 4N HCl using a general procedure

출처 및 근거

ORD 기록
ord-69dd6b55d4d649cf90285eb491d637a9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765779B2

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