Potassium Carbonate → ethyl (alphaS)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4'-ethoxymethyl-2',6'-dimethoxy(1,1'-biphenyl)-4-propionate

HRID 1454111ノート

反応式

HRID 1454111 の反応式
[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6])[CH3:3].[CH2:23]([O:25][CH2:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[C:30](B(O)O)=[C:29]([O:38][CH3:39])[CH:28]=1)[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN1CCCC1=O>[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:30]2[C:29]([O:38][CH3:39])=[CH:28][C:27]([CH2:26][O:25][CH2:23][CH3:24])=[CH:32][C:31]=2[O:33][CH3:34])=[CH:17][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6])[CH3:3]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 10236170(4-(Ethoxymethyl)-2,6-dimethoxyphenyl)boronic acidHCID 69597080N-Boc-4-bromo-L-phenylalanine ethyl ester

生成物 1

HCID 11329259ethyl (alphaS)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4'-ethoxymethyl-2',6'-dimethoxy(1,1'-biphenyl)-4-propionate収率 139.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

Under nitrogen atmosphere, a mixture of ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4-bromobenzene propanoate (11.17 g), 4-ethoxymethyl-2,6-dimethoxyphenylboronic acid (10.80 g), palladium acetate (0.34 g), triphenylphosphine (1.57 g), anhydrous potassium carbonate (12.44 g), N-methylpyrrolidone (56 ml) and water (11 ml) was stirred for 50 minutes at 80° C. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was washed with 10% aqueous citric acid solution and saturated aqueous NaCl solution, dried over magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure to yield ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate (20.4 g) as oil.

後処理

  1. customAfter completion of the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate and water
  4. washThe organic layer was washed with 10% aqueous citric acid solution and saturated aqueous NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-9897b36671f44fc89a04441963d359a2
出典データセット
uspto-grants-2009_01
特許番号
US07476758B2

反応ノート

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