Dimethylformamide → Methyl (2s,3s,5s)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

HRID 535085ノート

反応式

HRID 535085 の反応式
[C:1]([O:5][C@@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([OH:14])=O)[C@@H:8]([C:15]([O:17][CH3:18])=[O:16])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[C:1]([O:5][C@@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([N:28]2[CH2:29][CH2:30][N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)=[O:14])[C@@H:8]([C:15]([O:17][CH3:18])=[O:16])[CH2:7]1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67304647HCID 67304647、化合物

生成物 1

HCID 67304371Methyl (2s,3s,5s)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

実験手順

To a mixture of (2S,3S,5S)-5-tert-butoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid (43.0 mg, 0.000166 mol), 1-phenyl-piperazine (0.03166 mL, 0.0002073 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.09168 g, 0.0002073 mol) in N,N-dimethylformamide (0.40 mL, 0.0052 mol) was added N,N-diisopropylethylamine (0.03611 mL, 0.0002073 mol). The reaction was stirred at rt for 2 h, then quenched with water. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to dry. The residue was used directly in next step. MS (ESI): (M+H)+=404.2.

後処理

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry

出典と根拠

ORDレコード
ord-147f950d07c74dbaa44cf28e1d6bde62
出典データセット
uspto-grants-2014_10
特許番号
US08853243B2

反応ノート

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