4-Methylmorpholine → 1-[trans-4-(n-Tert-butoxycarbonylaminomethyl)-n-tert-butoxycarbonyl-l-prolyl]-4-(3-chloro-2-methylphenyl)piperazine

HRID 2185469노트

반응식

HRID 2185469 반응식
CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[C:20]([O:24][C:25]([NH:27][CH2:28][C@H:29]1[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:31]([C:41]([OH:43])=O)[CH2:30]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].Cl.[Cl:45][C:46]1[C:47]([CH3:58])=[C:48]([N:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)[CH:49]=[CH:50][CH:51]=1.ON1C2C=CC=CC=2N=N1>O1CCCC1.CN(C)C=O>[C:37]([O:36][C:34]([NH:32][CH2:33][C@H:29]1[CH2:28][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[C@H:31]([C:41]([N:55]2[CH2:54][CH2:53][N:52]([C:48]3[CH:49]=[CH:50][CH:51]=[C:46]([Cl:45])[C:47]=3[CH3:58])[CH2:57][CH2:56]2)=[O:43])[CH2:30]1)=[O:35])([CH3:40])([CH3:39])[CH3:38]

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 213415491-(1,1-Dimethylethyl) (2S,4S)-4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)-1,2-pyrrolidinedicarboxylateHCID 224584741-(3-Chloro-2-methylphenyl)piperazine hydrochloride

생성물 1

HCID 540742211-[trans-4-(n-Tert-butoxycarbonylaminomethyl)-n-tert-butoxycarbonyl-l-prolyl]-4-(3-chloro-2-methylphenyl)piperazine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

N-Methylmorpholine (60 μL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (94 mg) were added to a solution of trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-L-proline (Compound 109 (D), 120 mg), 1-(3-chloro-2-methylphenyl)piperazine hydrochloride (A, 128 mg) and 1-hydroxybenzotriazole (70 mg) in tetrahydrofuran (6 mL) and N,N-dimethylformamide (2 mL) at room temperature. After stirring at room temperature for 16 hr, the reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with saturated sodium hydrogen carbonate and brine. After drying over anhydrous sodium sulfate, the organic layer was concentrated in vacuo. The residue was washed with hexane to give the titled compound (98 mg) as a white powder: 1H NMR (400 MHz, ) δ 1.42-1.59 (18H), 1.80-2.00 (br s, 2H), 2.36 (s, 3H), 2.86 (br s, 4H), 2.98 (br s, 0.5H), 3.23 (br s, 2.5H), 3.60-3.80 (6 H), 4.68 (m, 1H), 6.89 (br m, 1H), and 7.11 (m, 2H); mass spectrum (EI+) m/e 511 (M).

후처리

  1. customthe reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid
  2. washThe organic layer was washed with saturated sodium hydrogen carbonate and brine
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. concentrationthe organic layer was concentrated in vacuo
  5. washThe residue was washed with hexane

출처 및 근거

ORD 기록
ord-11b4075cfb094ce3a614f027563a77ea
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399629B1

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