Cesium carbonate → Methyl O-(3'-amino-1,1'-biphenyl-3-yl)-N-triphenylmethyl-L-serinate

HRID 1265219노트

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HRID 1265219 반응식
C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[CH:22]=[C:23]([O:27][CH2:28][C@@H:29]([C:50]([O:52][CH3:53])=[O:51])[NH:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:24]=[CH:25][CH:26]=1.S(O)(O)(=O)=O.[NH2:59][C:60]1[CH:61]=[C:62](B(O)O)[CH:63]=[CH:64][CH:65]=1.NC1C=C(B(O)O)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.C1(C)C=CC=CC=1>[NH2:59][C:60]1[CH:65]=[C:64]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C@@H:29]([C:50]([O:52][CH3:53])=[O:51])[NH:30][C:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:22]=2)[CH:63]=[CH:62][CH:61]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 11773TriphenylarsineHCID 11329766Methyl O-(3-bromophenyl)-N-triphenylmethyl-L-serinateHCID 162111393-Aminophenylboronic Acid Hemisulfate

생성물 1

HCID 11353040Methyl O-(3'-amino-1,1'-biphenyl-3-yl)-N-triphenylmethyl-L-serinate

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매

실험 절차

Triphenyl arsine (0.31 g, 1.0 mmol, 0.1 equiv) and dichloro-bis(triphenylphosphine)-palladium(II) (0.35 g, 0.50 mmol, 0.05 equiv) were stirred under an argon atmosphere in DME (dimethoxy ethane; 56 mL) at rt for 30 min. Methyl O-(3-bromophenyl)-N-triphenylmethyl-L-serinate (Example 1) (5.16 g, 10.0 mmol, 1.0 equiv) and 3-amino phenyl boronic acid hemisulfate (2.2 g, 6.0 mmol, 1.2 equiv) were added as solids, followed by a 2M aqueous solution of cesium carbonate (15.0 mL, 30.0 mmol, 3 equiv). The reaction mixture was stirred for 3 h at rt and partioned between toluene and water. The organic layer was separated and dried over sodium sulfate. After filtration and evaporation of the solvents in vacuuo the crude product was purified by chromatography on SiO2 (gradient: toluene to toluene/-ethanol 97:3) Yield: 7.3 g, 39.0%. 1H NMR (CDCl3, 200 MHz) δ 7.65-7.40 (m, 10H); 7.25-7.12 (m, 11H); 6.97 (d, 2H); 4.70 (dd, 1H); 4.7 (dd, 1H); 3.75-3.65 (m, 3H); 3.24 (s, 3H); 2.90 (d, 1H). MS (DCI/NH3) 546 (M+NH4+), 529 (M+H); 234 (CPh3).

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration and evaporation of the solvents in vacuuo the crude product
  4. customwas purified by chromatography on SiO2 (gradient: toluene to toluene/-ethanol 97:3) Yield: 7.3 g, 39.0%

출처 및 근거

ORD 기록
ord-cce0981db5b44fe0bf6c13efc2754a9f
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545029B2

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