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

HRID 1265219ノート

反応式

HRID 1265219 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-cce0981db5b44fe0bf6c13efc2754a9f
出典データセット
uspto-grants-2003_04
特許番号
US06545029B2

反応ノート

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