Acetic Acid → Ethyl 1-[(2-ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}phenyl)methyl]-4-piperidinecarboxylate

HRID 1942652

반응식

HRID 1942652 반응식
[CH2:1]([C:3]1[C:10]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)=[N:13][CH:12]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)[CH3:2].C(O)(=O)C.C([O-])(=O)C.[Na+].[NH:39]1[CH2:44][CH2:43][CH:42]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:41][CH2:40]1>CO>[CH2:1]([C:3]1[C:10]([C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([C:26]([F:28])([F:29])[F:27])[CH:17]=3)=[N:13][CH:12]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][N:39]1[CH2:44][CH2:43][CH:42]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH2:41][CH2:40]1)[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 517045Sodium AcetateHCID 866590062-Ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}benzaldehyde

생성물 1

HCID 66981836Ethyl 1-[(2-ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}phenyl)methyl]-4-piperidinecarboxylate수율 187%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}benzaldehyde (D72) (64 mg), acetic acid (0.044 mL) and sodium acetate (62.6 mg) in methanol (10.00 mL) stirred under nitrogen at room temperature was added ethyl 4-piperidinecarboxylate (120 mg) in one charge. The reaction mixture was stirred at room temperature for 1 h, then the solvent was evaporated in vacuo. The residue was dissolved in dichloromethane (DCM) (10 mL), sodium triacetoxyborohydride (97 mg) was added to the mixture. The reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate (100 mL) and saturated brine (30 mL). The organic phase was dried over sodium sulphate and evaporated in vacuo to give the crude product ethyl 1-[(2-ethyl-3-{2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}phenyl)methyl]-4-piperidinecarboxylate (D81) (160 mg). The crude product was used for next step without further purification. MS (ES): C30H35F3N2O3S requires 560. found 561.3 (M+H+).

후처리

  1. additioncharge
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (DCM) (10 mL)
  4. additionsodium triacetoxyborohydride (97 mg) was added to the mixture
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and saturated brine (30 mL)
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-d09b3e41f482432b91690b63b7bf8a24
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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