Potassium Carbonate → (S)-tert-Butyl 2-((S)-1-amino-3-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

HRID 600326

반응식

HRID 600326 반응식
[NH2:1][C:2](=[O:36])[C@@H:3]([NH:20][C:21]([C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1.Br[C:38]1[CH:39]=[CH:40][C:41]2[O:45][C:44](=[O:46])[N:43]([CH3:47])[C:42]=2[CH:48]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[NH2:1][C:2](=[O:36])[C@@H:3]([NH:20][C:21]([C@@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1[C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])=[O:22])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:38]2[CH:39]=[CH:40][C:41]3[O:45][C:44](=[O:46])[N:43]([CH3:47])[C:42]=3[CH:48]=2)=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 3374695-bromo-3-methyl-3H-benzooxazol-2-oneHCID 57999680(S)-tert-Butyl 2-((S)-1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)piperidine-1-carboxylate

생성물 1

HCID 57999664(S)-tert-Butyl 2-((S)-1-amino-3-(4-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate수율 95.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
75 °C

실험 절차

A mixture of (S)-tert-butyl 2-((S)-1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)piperidine-1-carboxylate (113 mg), 5-bromo-3-methylbenzo[d]oxazol-2(3H)-one (51.4 mg), [1,1′-bis[bis(1,1-dimethylethyl)phosphino-κP]ferrocene]dichloro palladium (7.34 mg) and potassium carbonate (93 mg) in acetonitrile (0.7 mL) and water (0.35 mL) was stirred at 75° C. for 2 h. The solvent was removed in vacuo and the residue was purified by flash silica chromatography eluting with 1:1 isohexane/acetone to give the subtitle compound (112 mg).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash silica chromatography
  3. washeluting with 1:1 isohexane/acetone

출처 및 근거

ORD 기록
ord-192e526ee52f4bd4866ceecd7916be5b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902181B2

연결된 노트

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