Sodium Hydroxide → HCID 86700874, 화합물

HRID 881769노트

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HRID 881769 반응식
[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[O:29][C:26]([CH2:30][C:31]([O:33]C)=[O:32])([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[O:29][C:26]([CH2:30][C:31]([OH:33])=[O:32])([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 86700875HCID 86700875, 화합물

생성물 1

HCID 86700874HCID 86700874, 화합물수율 49%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-(4-(4′-((5-(tert-butyl)-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-7-oxabicyclo[2.2.1]heptan-1-yl)acetate (110 mg, 0.24 mmol) in THF (4 mL) and Methanol (1 mL) was added 1N NaOH (0.72 mL, 0.72 mmol) and the reaction was let stir at rt for 2 hr. The resulting yellow reaction mixture was partially concentrated by rotary evaporation in vacuo (rt water bath). The yellow solution was diluted with MeOH, filtered and purified on preparative HPLC (10-50% MeCN:5 mM NH4OH) to afford 52 mg (49%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (s, 9H), 1.63-1.82 (m, 4H), 1.90-2.02 (m, 2H), 2.08-2.21 (m, 2H), 2.79 (s, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.56-7.70 (m, 6H), 10.51 (br. s., 1H). ESI-MS m/z: 448.1 [M+H]+, retention time 1.08 min (condition E). HR/MS [M+H]+: found 448.2236. calc. 448.2218. RT: 2.27 (Condition L).

후처리

  1. concentrationThe resulting yellow reaction mixture was partially concentrated by rotary evaporation in vacuo (rt water bath)
  2. additionThe yellow solution was diluted with MeOH
  3. filtrationfiltered
  4. custompurified on preparative HPLC (10-50% MeCN:5 mM NH4OH)

출처 및 근거

ORD 기록
ord-4497d9c679a44d158793769bbf1568af
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993619B2

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