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

HRID 61473ノート

反応式

HRID 61473 の反応式
[CH3:1][O:2][C@@H:3]1[CH2:8][NH:7][C@H:6]([C:9]([OH:11])=O)[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:4]1.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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>>[CH3:1][O:2][C@@H:3]1[CH2:8][NH:7][C@H:6]([C:9]([N:25]2[CH2:26][CH2:27][N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][CH2:24]2)=[O:11])[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:4]1

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67305316(2s,3s,5s)-5-Methoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

生成物 1

HCID 67304478Methyl (2s,3s,5s)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

実験手順

To a mixture of (2S,3S,5S)-5-methoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid (14.0 mg, 0.0000644 mol), 1-phenyl-piperazine (0.01231 mL, 8.056E-5 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (35.63 mg, 8.056E-5 mol) in N,N-dimethylformamide (0.20 mL, 0.0026 mol) was added N,N-diisopropylethylamine (0.01403 mL, 8.056E-5 mol). The mixture was stirred at rt for 2 h. After quenched with water, the mixture was extracted with ethyl acetate. The combine organic lyers were washed with brine, dried and concentrated to dry. The residue was used directly in next step without further purification. MS (ESI): (M+H)+=362.1.

後処理

  1. customAfter quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combine organic lyers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry
  7. customThe residue was used directly in next step without further purification

出典と根拠

ORDレコード
ord-8a028f4803844a06b97490d17c5d9695
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

反応ノート

読み込み中…