Triethylamine → Methyl 3-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxycarbonylamino]piperidin-1-yl]benzoate

HRID 602190ノート

反応式

HRID 602190 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]2[CH2:19][CH2:18][CH2:17][CH:13](C(O)=O)[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.C([N:39]([CH2:42]C)CC)C.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[S:52][C:53]([CH2:57][OH:58])=[C:54]([CH3:56])[N:55]=2)=[CH:47][CH:46]=1>C1C=CC=CC=1.O>[Cl:44][C:45]1[CH:46]=[CH:47][C:48]([C:51]2[S:52][C:53]([CH2:57][O:58][C:42]([NH:39][CH:13]3[CH2:17][CH2:18][CH2:19][N:11]([C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:3]([O:2][CH3:1])=[O:4])[CH2:12]3)=[O:27])=[C:54]([CH3:56])[N:55]=2)=[CH:49][CH:50]=1

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 199401P,P-Diphenylphosphinic azideHCID 27636922-(4-Chlorophenyl)-4-methyl-5-thiazolemethanolHCID 589926191-[3-(Methoxycarbonyl)phenyl]nipecotic acid

生成物 1

HCID 58992614Methyl 3-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxycarbonylamino]piperidin-1-yl]benzoate収率 52%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

1-[3-(Methoxycarbonyl)phenyl]nipecotic acid (105 mg, 0.400 mmol) was suspended in benzene (8 mL). To this suspension, diphenylphosphoryl azide (0.0948 mL, 0.440 mmol) and triethylamine (0.0615 mL, 0.440 mmol) were added and the mixture was stirred for 2 hours while being refluxed. Subsequently, 2-(4-chlorophenyl)-4-methylthiazol-5-yl methanol (105 mg, 0.440 mmol) and triethylamine (0.0615 mL, 0.440 mmol) were added and the mixture was further stirred for 6 hours while refluxed. Water was then added and the mixture was extracted with ethyl acetate. The extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine. This was followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 103 mg (52%) of the desired compound as a colorless powder.

後処理

  1. temperaturewhile being refluxed
  2. stirringthe mixture was further stirred for 6 hours
  3. temperaturewhile refluxed
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  7. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

出典と根拠

ORDレコード
ord-b42a8753ec3e42ccbddc3c7f6c4617f1
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

読み込み中…