Veratrylamine → 1,1-Dimethylethyl 4-[{4-(benzyloxy)-2-[(3,4-dimethoxybenzyl)carbamoyl]phenyl}(isobutoxycarbonyl)amino]piperidine-1-carboxylate

HRID 80463

반응식

HRID 80463 반응식
[Na].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:19]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])=[C:14]([CH:18]=1)[C:15](O)=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:73]([NH2:84])[C:74]1[CH:83]=[CH:82][C:79]([O:80][CH3:81])=[C:76]([O:77][CH3:78])[CH:75]=1>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:19]([C:20]([O:22][CH2:23][CH:24]([CH3:25])[CH3:26])=[O:21])[CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[C:14]([C:15](=[O:16])[NH:84][CH2:73][C:74]2[CH:83]=[CH:82][C:79]([O:80][CH3:81])=[C:76]([O:77][CH3:78])[CH:75]=2)[CH:18]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 5

HCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 5360545SodiumHCID 595871175-(Benzyloxy)-2-({1-[(1,1-dimethylethoxy)carbonyl]piperidin-4-yl}[(2-methylpropoxy)carbonyl]amino)benzoic acid

생성물 1

HCID 666037821,1-Dimethylethyl 4-[{4-(benzyloxy)-2-[(3,4-dimethoxybenzyl)carbamoyl]phenyl}(isobutoxycarbonyl)amino]piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 6 g of sodium salt of 5-(benzyloxy)-2-({1-[(1,1-dimethylethoxy)carbonyl]piperidin-4-yl}[(2-methylpropoxy)carbonyl]amino)benzoic acid obtained in stage 1.3 and 4.42 g of DIEA in 250 ml of DMF is stirred at AT for 15 min. 6.48 g of HBTU are added and the mixture is left stirring for 30 min. 2.48 g of veratrylamine are added and the reaction mixture is stirred for 48 h 00. It is evaporated under reduced pressure, the residue is taken up in AcOEt, washed with a saturated NH4Cl solution and with a saturated NaHCO3 solution, dried over Na2SO4 and filtered, and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (20/80, v/v) as far as (60/40, v/v), to give 7.5 g of expected product.

후처리

  1. waitthe mixture is left
  2. stirringstirring for 30 min
  3. stirringthe reaction mixture is stirred for 48 h 00
  4. customIt is evaporated under reduced pressure
  5. washwashed with a saturated NH4Cl solution and with a saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent is evaporated under reduced pressure
  9. customThe residue is chromatographed on silica gel, elution

출처 및 근거

ORD 기록
ord-ef7fdc0c79504a6f83b11d3ddad648fd
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846654B2

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