Sodium Carbonate → (S)-4'-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-4-yl methanesulfonate

HRID 216918노트

반응식

HRID 216918 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.[CH3:30][S:31]([O:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:30][S:31]([O:34][C:35]1[CH:36]=[CH:37][C:38]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C@H:3]([NH:12][C:13]([C:15]3([NH:21][C:22]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:28])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:14])[C:2]([NH2:1])=[O:29])=[CH:6][CH:7]=2)=[CH:39][CH:40]=1)(=[O:33])=[O:32]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 441185724-(Methylsulfonyloxy)phenylboronic acidHCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

생성물 1

HCID 59568621(S)-4'-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-4-yl methanesulfonate수율 72%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

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), 300 mg) in acetonitrile (7 mL) under nitrogen was treated with 4-(methylsulfonyloxy)phenylboronic acid (125 mg) followed by aqueous sodium carbonate (2M, 0.58 mL). Nitrogen was bubbled through the mixture and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added. The mixture was stirred at 85° C. for 25 h. The solvent was partially evaporated and then purified by chromatography on silica using ethyl acetate 50-100% isohexane as eluent to afford the sub-titled compound as a white solid (234 mg).

후처리

  1. customNitrogen was bubbled through the mixture and 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (5 mg)
  2. additionwas added
  3. customThe solvent was partially evaporated
  4. custompurified by chromatography on silica

출처 및 근거

ORD 기록
ord-4aabba31b8344cb68096fc3d624b8591
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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