Potassium Carbonate → HCID 53892462、化合物

HRID 24693ノート

反応式

HRID 24693 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[C:5]([O:27][CH3:28])[C:4]=1B(O)O.[CH2:32]([O:34][C:35](=[O:56])[C@H:36]([CH2:48][C:49]1[CH:54]=[CH:53][C:52](Br)=[CH:51][CH:50]=1)[NH:37][C:38](=[O:47])[C:39]1[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:46])[CH3:33].C([O-])([O-])=O.[K+].[K+]>COCCOC.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:32]([O:34][C:35](=[O:56])[C@H:36]([CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:4]2[C:5]([O:27][CH3:28])=[CH:6][C:7]([OH:9])=[CH:8][C:3]=2[O:2][CH3:1])=[CH:51][CH:50]=1)[NH:37][C:38](=[O:47])[C:39]1[C:40]([Cl:46])=[CH:41][CH:42]=[CH:43][C:44]=1[Cl:45])[CH3:33]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 225718572,6-Dimethoxy-4-(tert-butyl-diphenylsilyloxy)benzeneboronic acidHCID 54106344(S)-Ethyl 3-(4-bromophenyl)-2-(2,6-dichlorobenzamido)propanoate

生成物 1

HCID 53892462HCID 53892462、化合物収率 53.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2,6-dimethoxy-4-(tert-butyl-diphenylsilyloxy)benzeneboronic acid (3 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester (0.8 g), Pd(PPh3)4 (1 g) and K2CO3 (2.1 g) in DME/H2O (20 mL/0.5 mL) was heated at 80° C. for 6 hour under N2. The mixture was diluted with EtOAc and washed with water, dried and evaporated. The residue was dissolved in EtOAc and the solution was filtered through a silica gel column and evaporated. The residue was dissolved in THF, and TBAF (1.6 M in THF, 4 ml) was added. The mixture was stirred at room temperature for 1 hour, diluted with water and extracted with EtOAc. The extract was washed with water, dried and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1/2) to yield 0.5 g of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-4-hydroxyphenyl)-L-phenylalanine ethyl ester. ESMS m/z: 490 (MH+).

後処理

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. filtrationthe solution was filtered through a silica gel column
  6. customevaporated
  7. dissolutionThe residue was dissolved in THF
  8. additionTBAF (1.6 M in THF, 4 ml) was added
  9. additiondiluted with water
  10. extractionextracted with EtOAc
  11. washThe extract was washed with water
  12. customdried
  13. customevaporated
  14. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1/2)

出典と根拠

ORDレコード
ord-410ad7b90dea4035828019e4f37d1412
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

反応ノート

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