Triethylamine → 3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butyl 1,2,3,4-tetrahydro-5-naphthoate

HRID 844586ノート

反応式

HRID 844586 の反応式
[CH2:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11](Cl)=[O:12])[C:5]=2[CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:16]=[C:17]([C@@H:22]([CH2:26][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[CH2:23][CH2:24][OH:25])[CH:18]=[CH:19][C:20]=1[Cl:21].C(N([CH2:37][CH3:38])CC)C>C(#N)C>[CH2:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:25][CH2:24][CH2:23][C@@H:22]([C:17]3[CH:18]=[CH:19][C:20]([Cl:21])=[C:15]([Cl:14])[CH:16]=3)[CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[C:11]([C:6]3[C:5]4[CH2:4][CH2:3][CH2:2][CH2:1][C:10]=4[CH:9]=[CH:37][CH:38]=3)=[O:12])=[O:12])[C:5]=2[CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27531625,6,7,8-Tetrahydronaphthalene-1-carbonyl chlorideHCID 541546783(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol

生成物 1

HCID 598865763(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butyl 1,2,3,4-tetrahydro-5-naphthoate収率 72.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1,2,3,4-Tetrahydro-5-naphthoyl chloride (1.70 g) (see Preparation 36) was added dropwise to a suspension of 3(S)-(3,4-dichlorophenyl)-4-(imidazol-1-yl)butan-1-ol (0.90 g) (see Preparation 99) and triethylamine (1.45 g) in anhydrous acetonitrile (15 ml) and the solution stirred at room temperature for 4 days. The solvent was then removed under reduced pressure to give a residue which was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The phases were separated and the aqueous phase further extracted with ethyl acetate. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with a solvent gradient of 2:1 changing to 0:1, by volume, pentane:ethyl acetate to give 3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butyl 1,2,3,4-tetrahydro-5-naphthoate (1.38 g) as a gum.

後処理

  1. customThe solvent was then removed under reduced pressure
  2. customto give a residue which
  3. customwas partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  4. customThe phases were separated
  5. extractionthe aqueous phase further extracted with ethyl acetate
  6. washwashed sequentially with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe solvent removed under reduced pressure
  9. customto give a residue which
  10. customwas chromatographed on silica gel eluting with a solvent gradient of 2:1 changing to 0:1, by volume, pentane

出典と根拠

ORDレコード
ord-4627fdfaa35f42d9bc4f3a25e943b8eb
出典データセット
uspto-grants-2002_04
特許番号
US06380396B1

反応ノート

読み込み中…