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

HRID 602190노트

반응식

HRID 602190 반응식
[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

참가 물질

7

반응물 4

HCID 8471Triethylamine2회HCID 199401P,P-Diphenylphosphinic azideHCID 27636922-(4-Chlorophenyl)-4-methyl-5-thiazolemethanolHCID 589926191-[3-(Methoxycarbonyl)phenyl]nipecotic acid

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b42a8753ec3e42ccbddc3c7f6c4617f1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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