Methanol → (+/-)-5-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, ethyl ester

HRID 324394

反応式

HRID 324394 の反応式
[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[NH:22][CH:23]=3)[C:6]=2[N:7]=1)[CH3:2].C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[CH2:41]([O:43][C:44]([C:46]1[O:47][C:48]([CH2:51]Br)=[CH:49][CH:50]=1)=[O:45])[CH3:42].CO>ClCCCl.C(#N)C>[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[N:22]([CH2:51][C:48]4[O:47][C:46]([C:44]([O:43][CH2:41][CH3:42])=[O:45])=[CH:50][CH:49]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2]

参加物

7

反応物 4

HCID 887MethanolHCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 137895295-Bromomethyl-2-furancarboxylic acid ethyl esterHCID 70112980(+/-)-5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

生成物 1

HCID 131722500(+/-)-5-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, ethyl ester

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6342Acetonitrile溶媒

実験手順

To a slurry of the product of step (vii) (1.42 g) in dry 1,2-dichloroethane (15 ml) was added bis(trimethylsilyl)trifluoroacetamide (3.4 ml). The mixture was heated at reflux for 2 hours until the mixture became a homogeneous solution. The solution was allowed to cool to room temperature and a solution of 5-[bromomethyl]-2-furancarboxylic acid ethyl ester (J. Chem. Soc. Perkin Trans. 1, 1981, 1125, Bull. Chem. Soc. Jpn., 1987, 60, 1807) (1.1 g) in dry acetonitrile (15 ml) was added. The solution was then heated at reflux for 14 hours. The reaction mixture was allowed to cool and methanol (15 ml) was added. The solvents were evaporated under reduced pressure and the residue was triturated with diethyl ether. The resultant solid was collected by filtration and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic phase was dried (MgSO4) and the solvent was evaporated under reduced pressure. Purification was by chromatography eluting with ethyl acetate.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours until the mixture
  3. temperatureThe solution was then heated
  4. temperatureat reflux for 14 hours
  5. temperatureto cool
  6. customThe solvents were evaporated under reduced pressure
  7. customthe residue was triturated with diethyl ether
  8. filtrationThe resultant solid was collected by filtration
  9. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  10. dry with materialThe organic phase was dried (MgSO4)
  11. customthe solvent was evaporated under reduced pressure
  12. customPurification
  13. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-ae78dad7c2fa441ab41b357c8b256f7d
出典データセット
uspto-grants-2001_04
特許番号
US06218376B1

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