Sodium Carbonate → (S)-tert-Butyl 4-(1-amino-3-(3'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216922노트

반응식

HRID 216922 반응식
[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[C:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)#[N:31].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([C:30]#[N:31])[CH:37]=2)=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

생성물 1

HCID 59568564(S)-tert-Butyl 4-(1-amino-3-(3'-cyanobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate수율 95.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
85 °C

실험 절차

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 350 mg) in acetonitrile (7 mL) under nitrogen was treated with 3-cyanophenylboronic acid (99 mg) followed by aqueous sodium carbonate (2M, 0.677 mL). Nitrogen was bubbled through and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (10 mg) was added. The mixture was stirred at 85° C. for 25 h. The solvent was partially evaporated and the solution was purified by chromatography on silica using 50% ethyl acetate in isohexane and then ethyl acetate as eluent to afford the sub-titled compound as a solid (316 mg).

후처리

  1. customNitrogen was bubbled through and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (10 mg)
  2. additionwas added
  3. customThe solvent was partially evaporated
  4. customthe solution was purified by chromatography on silica using 50% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-a197af4afc5a4f65ad23f786d3ff55c5
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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