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4-Methylmorpholine → (S)-N-((S)-6-Cyano-1,2,3,4-tetrahydroquinolin-3-yl)-2-hydroxy-2-phenylacetamide

HRID 2234246
ノート
印刷プレビュー

反応式

HRID 2234246 の反応式
Cl.Cl.[NH2:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]#[N:15])[CH:11]=2)[NH:6][CH2:5]1.[C:16](O)(=[O:25])[C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[C:14]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH2:5][C@@H:4]([NH:3][C:16](=[O:25])[C@@H:17]([OH:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:13]2)#[N:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 439616(S)-mandelic acidHCID 1317281063-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile, dihydrochloride

生成物 1

HCID 66757271(S)-N-((S)-6-Cyano-1,2,3,4-tetrahydroquinolin-3-yl)-2-hydroxy-2-phenylacetamide
収率 20%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile, dihydrochloride (10.03 g, 40.7 mmol), prepared as described in Example 1D, in DMF (100 mL) was added (S)-(+)-mandelic acid (7.45 g, 48.9 mmol), followed by EDAC (9.37 g, 48.9 mmol), HOBt (7.49 g, 48.9 mmol) and NMM (16.1 mL, 146.1 mmol). The reaction mixture was stirred at RT overnight, then diluted with EtOAc (200 mL), washed with water (50 mL×3), 1N aqueous HCl (50 mL), water (50 mL) and saturated aqueous NaCl, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc/hexanes (2:1 ratio), and the purified compound crystallized from acetone three times to give the title compound as the (S, S) diastereoisomer (2.54 g, 20% yield).

後処理

  1. washwashed with water (50 mL×3), 1N aqueous HCl (50 mL), water (50 mL) and saturated aqueous NaCl
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed (silica gel)
  5. washeluting with EtOAc/hexanes (2:1 ratio)
  6. customthe purified compound crystallized from acetone three times

出典と根拠

ORDレコード
ord-a9cdcd927e9847e99be9f3ee2cb12dad
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709647B2

反応ノート

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