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

HRID 2185469ノート

反応式

HRID 2185469 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-11b4075cfb094ce3a614f027563a77ea
出典データセット
uspto-grants-2002_06
特許番号
US06399629B1

反応ノート

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