Triethylamine → N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinamide

HRID 1744141노트

반응식

HRID 1744141 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:21]([CH3:34])=[N:22][O:23][C:24]=3[NH:25][C@H:26]([C:31]([OH:33])=O)[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](O[N:52]2N=[N:59][C:54]3C=CC=C[C:53]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:53]([CH2:54][NH:59][C:31](=[O:33])[C@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:25][C:24]1[O:23][N:22]=[C:21]([CH3:34])[C:20]=1[C:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[CH:19][CH:18]=1)#[N:52]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69152769N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucine

생성물 1

HCID 86594577N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To N-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucine (415 mg, 0.879 mmol), PyBOP (505 mg, 0.97 mmol), aminoacetonitrile hydrochloride (179 mg, 1.93 mmol) in dry DMF (15 mL) under dry nitrogen was added triethylamine (0.44 mL, 3.1 mmol) dropwise and the reaction was stirred for 3 hours. Aqueous sat. NaHCO3 was added and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 6/4) to afford N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-3-methylisoxazol-5-yl)leucinamide.

후처리

  1. extractionthe product extracted with Et2O (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 6/4)

출처 및 근거

ORD 기록
ord-2ea8ff9764794ec1bca5e8433322ff05
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07012075B2

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